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I should have been more complete in my initial post on the other thread but it is a subject that troubles me.

Let me start by answering JAFO's question about my daughters preferring the real estate. My daughter doesn't have a preference for my land. She and her husband have done very well for themselves and frankly it would be easier for her just to get a big slice of investment accounts and not have to deal with the real estate.

But she is far and away the most responsible and sensible of the two, so she is the best choice for executor. But if she doesn't own the real estate by inheriting it 100%, then her brother will be circling, agitating for a quick sale, any sale to he can get his 50%.
And she may very well decide to keep the real estate for an investment, make it a rental, or split the acreage, and sell that off in lots or as one or more big chunks, and keep the house for herself or a rental. Anyway, she can sort all that out at her leisure if she is sole owner.

As far as other personal property, I do plan of letting them choose what they want ahead of time. Some of it is just stuff that needs to be sold, e.g. I have three trucks and a tractor that I am pretty sure neither one of them will call dibs. So these end up in the unclaimed pool which along with all the other misc unclaimed stuff, I want to go to only one of them and that one needs to be my daughter. If it is my son, then he would have a lot of his property that is setting inside his sister’s house which then needs to be removed which leads to conflict. FWIW, the value of all that misc stuff is tiny compared to the real estate and investment accounts anyway.

My investment accounts are easy to split but here is where I am conflicted. Let’s say my land is worth $1.5M and I have $2.0M in investments at the time I die. So I could make the estate a more or less even split by leaving my son $1.75M in investments and my daughter $1.5M in real estate and $250K in investments, they both get more or less $1.75M that way.

My daughter has worked hard along with her husband, both LYBM, working two jobs, paying of their home early, buying a rental property, paying that off, starting and running a very successful internet business while still holding down a full time job. They are doing great but have worked hard to get there. Two grandsons, nice house in the suburbs, no debt.

Meanwhile, my son went to law school, earned big bucks quickly, decided he didn't like working, quit his job, divorced his wife, and literally was living in an RV as he traveled aimlessly around the country, going to concerts, Burning Man, living in state parks for weeks at a time, then moving on, a ner-do-well vagabond. Then he got in trouble with the law for reasons that are too embarrassing to talk about, but not murder or anything like that, and presently is in prison.

So you maybe can understand why my daughter is the best choice for executor and the one who will deal responsibly with disposal of assets. When my son gets out of prison, he certainly will need money since he likely will be unemployable. But he would rather not work anyway which bugs me.

This is where my conflict comes in. Does he deserve an equal slice since he has been so irresponsible? I am not saying I would cut him out but I really don't feel good about an equal slice either. And I do have two grandsons, so they would benefit from my daughter having more assets to eventually leave to them.

So there you have it. I had not planned on getting into all this detail, especially the dirty laundry, but now that I have, any advice or observations that you or anyone else on the board would care to offer would be most welcome. Like I said I am conflicted and have been so for quite some time and I need to come to grips with it.
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any advice or observations that you or anyone else on the board would care to offer would be most welcome

Well...the son won't appreciate it, and will likely p..s it away. While the daughter doesn't need it, and giving it to her would antagonize the son. How about skipping a generation and leaving it all in trust for the grandkids? Should son have a child in the future, perhaps the trust would allow for that?

Or, a step further, leave it all to your favorite charity?

Just random thoughts, which I'm working through for my own family.

Tim
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You could also leave the son his inheritance in a separate trust that is paid to him in installments. I know of a situation where the the original trust was split into new trusts, one for each heir, and is paid out in equal installments over the next ten years.

Tough decisions.

Or you could go wild and spend it all.

gcr
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I am following Dad's path.

He sold the family household, put all of his money into economic assets, instructed me to disburse 1/3 each to each of his three sons. No real estate to sell, no discussion of who did or did not deserve what, no discussion of who would or would not manage their assets well or not.

The only wrinkle was that my middle brother died before Mom and Dad, so I was instructed to leave my middle brother's portion equally to his 4 sons.

We were all treated fairly and equally, and nobody b!tched about me following Dad's will and Trust documents to the letter.

In your case, the daughter will likely have more than enough to live on, and your son will not. But they both will have been fairly and equally treated, and their destiny will be of their own making.

Just one way to do it.
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Bighairymike,

Obviously, in the end, you have to make that decision. In the meantime, I can relate my situation - from a son's perspective. :)

Ironically, I am the son who is like your daughter. And, my sister is like your son. Early on she had very little, then married in her 40s and they did okay. BUT, in Dad's mind, she would give away money to anyone asking for it. Dad did not want "his" money (an estate worth about $1.2MM)to go to scammers. Basically, he wanted to control his money from the grave. Mom wanted to split the estate 50-50, but Dad wanted to cut my sister out completely.

As the "responsible" son who moved half way across the country to be near them during their final years, I was the Executor which was fine with me. They both did their wills and POAs several years in advance of their passing.

Mom died first. Before dad died 6 months later, he told me he was considering cutting my sister out completely. He asked me if I was ok with it. I told him that, as Executor, my job was to follow his wishes. I knew it might be a problem, but it would be his call.

In the end, I think out of respect for his spouse, he did not change his will to cut out my sister. Upon his passing, my sister drove from Florida to NY, looked around the house for 30 minutes for anything she might be interested in, and promptly left. She said "Whatever you want to do."

My sister got her 50%. Would she have contested the will if she got nothing, I don't know and did not care. My job would be to perform the job of the Executor.

Luckily, I will not have to face the your dilemma because we have no kids. There is a biblical story - the Prodigal Son - that might help you.

Ironically enough, this might help you. My estate is about the size of yours and our plan is to give it all to charity. I have found that I need to let go of my need to see the donation spent well and simple make the donation - hoping it will be used wisely. Doing anything else is like "controlling from the grave" which is a waste of time.

So, in the end, my suggestion is to give to both - factoring in your daughter's executor work and the grandkids. Then, simply ask your son to use his inheritance in a manner that respects your philosophy. Then, let it go.

Hope this helps a bit. Best,

PW
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Meanwhile, my son went to law school, earned big bucks quickly, decided he didn't like working, quit his job, divorced his wife, and literally was living in an RV as he traveled aimlessly around the country, going to concerts, Burning Man, living in state parks for weeks at a time, then moving on, a ner-do-well vagabond. Then he got in trouble with the law for reasons that are too embarrassing to talk about, but not murder or anything like that, and presently is in prison.

I too suggest a trust. It can protect the assets from debtors and lawsuits. You can have someone manage the trust, have the income pass through the trust to your son, and then at his death it can either pass to your daughter or remain in trust for her kids or go to charity. You can set it up in a variety of ways, and I suggest talking with an attorney who handles wills and trusts to set this up.

We have a trust set up for our kids, mostly as a safeguard against them inheriting too much too young if we get hit by a semi while driving down the interstate. We chose to give them the option of dissolving the trust at 35, but they have the right to retain it if it is to their benefit to do so, (divorce or lawsuit comes to mind.) There is real estate in the trust, which we have in there as subject to sale and division of proceeds, or they can buy the property from their share of the trust at a price set by appraisal, the property remaining in the trust for their use until they get it at 35.

You can set up the trust in almost any way imaginable. A lawyer can guide you.

DH is also a recipient of a nightmare of a trust. Binder of documents is so big and complicated that it was hard to get anyone to be co-trustee with him as required, particularly given the very small size of the trust. Keep it as simple as possible and documentation to a minimum.

IP
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Does he deserve an equal slice since he has been so irresponsible?

Yes.

Your situation has similarities to my family's:
- I'm The Responsible One, and have children and a grandchild.
- One of my brothers was in prison for 15 years, during which time Dad visited an estate planning attorney and made his plans. (Bro never married, and as far as we know has no children.)
- I also have many other siblings, some of whom also have children and grandchildren, so that's a little more complicated than your family, but not really relevant here.

Dad's documents state that when he dies, all his assets will be divided equally among all his children, which I think is the best way to do it. Regardless of who deserves what, we are all equally his children, and he loves us all.
Will felon bro blow through his inheritance? Most likely, but IMO better he receive it and blow through it, than feel he's been shortchanged, and bug me for what he considers his fair share that I unfairly received and don't need.

Regarding the logistics of distributing the estate:

- A Trust will be created for each of the adult children. Assets will be divided, and an equal amount deposited to each Trust.

- I will be Trustee of my Trust, so I can do pretty much whatever I want with it.

- Dad doesn't want Bro to be Trustee of his own Trust, because he'd rather the assets not be spent on drugs or otherwise wasted. So, at the estate planning attorney's suggestion, a neutral 3rd party will be Trustee, namely, someone from Dad's credit union's Trust Department.
I have no idea what the procedures will be for Bro to request money from his Trust, or for the Trustee to disperse the funds. I'm guessing the Trustee will approve rent money but not drugs; but money is fungible, so it's a mystery to me how any Trustee can ensure the money will go only to good causes. Maybe the Trustee will simply send Bro an allowance, to be paid monthly until the money runs out?

- Since Dad's house and cars have all already been sold, all his remaining assets are liquid. So theoretically it should be simple to divide, but at 96 Dad's still chugging along, so we haven't crossed that bridge yet.

- If Dad still had a house, then at his death I'd get it appraised. If any of my siblings wanted to keep it, for whatever reason, then its value would come out of their share of the liquid assets. Depending on the values of the house vs other assets, they might have to bring money to the table to buy the other siblings out. It would be an algebra problem, pretty straightforward IMO. I'd let Dad's attorney handle as much of it as possible.

- It's good to plan for your demise, but there may well be many years before that where you'll need help. Starting when Dad was in his mid-80's, I helped with bill-paying, hiring housekeepers, later hiring caregivers, making medical decisions, etc. Dad's having named me POA, medical POA, and Trustee was a huge help in my ability to get things done.

So that's where Dad's affairs stand. I think you'd be well served by consulting with a good estate planning attorney (alas, you might have to interview several before finding one you like, but that's similar to anyone else you hire).
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...I do have two grandsons, so they would benefit from my daughter having more assets to eventually leave to them....

DH's and my estate will be left equally to each of our children, one of whom is married with a baby, the other of whom is single and childless, and will likely remain so.

Meanwhile, we contribute monthly to the grandchild's 529. If more grandchildren arrive, we'll contribute to theirs also.

It's typical to leave assets to just the children, but a variation where some is left to children and some to grandchildren is also valid. I, personally, feel the latter arrangement would be too complicated and has the potential of making the childless heirs feel shortchanged. So my preference is to "give with warm hands" to the grandchildren.
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Well...the son won't appreciate it, and will likely p..s it away. While the daughter doesn't need it, and giving it to her would antagonize the son. - Wyomingtim

That IS the essence of it right there.

How about skipping a generation and leaving it all in trust for the grandkids?

Frankly I never considered that except indirectly though my daughter. I have somewhat of an irrational aversion to trusts, too complicated or subject to revisions in law, but I will give that some serious thought.

Thanks.
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... irrational aversion to trusts, too complicated ...

Not irrational at all. Trusts were too complicated, and each lawyer created his own, there was no standard.
Now there's a uniform (for the USA) Trust standard, with slight variations depending on state, and more potential variations based on individual's circumstances and wishes.

Still not a magic wand, but worth considering, even if you do ultimately decide that a simple will combined with POD's is your best course.
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I agree with one of nothingissimple's options: leave your assets to a charity or foundation, Planned Parenthood, St. Jude's, whatever.

Your daughter doesn't need your assets; your son doesn't deserve them and only would misuse them. Avoid the problem of favoring one child over the other.

Pete
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Well...the son won't appreciate it, and will likely p..s it away.

On the other hand, you'll be gone and why should you care how he spends it? It's his life...

Tim
who p..sed away quite a few years of his youth, and had a heck of a time doing it.
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On the other hand, you'll be gone and why should you care how he spends it? It's his life... - Wyomingtim

------------------------

True, but in the period between setting up my estate plan and the time I die, I will have the knowledge that I passed up a lot of things in life that I would have enjoyed with the result being him p..sing it away. In other words, if I wanted it pissed away, I would have done it myself. I would have that to think about for the next fifteen or twenty tears.

But I realize that sort of thinking is what is causing the indecision I now wrestle with. Thanks to all who provided ideas and personal experiences. I will read this thread again and maybe a few times more as I contemplate a course of action which will be least stressful.

Concerning seeing an estate planning attorney: I always knew this would be necessary to draw up and make legal a general plan I already have developed. Would it be productive to go to one with all the loose ends and unresolved issues I have expressed here. The issues I have are more philosophical than legal.
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bighairymike: "I should have been more complete in my initial post on the other thread but it is a subject that troubles me.

. . .

As far as other personal property, I do plan of letting them choose what they want ahead of time. Some of it is just stuff that needs to be sold, e.g. I have three trucks and a tractor that I am pretty sure neither one of them will call dibs. So these end up in the unclaimed pool which along with all the other misc unclaimed stuff, I want to go to only one of them and that one needs to be my daughter. If it is my son, then he would have a lot of his property that is setting inside his sister’s house which then needs to be removed which leads to conflict. FWIW, the value of all that misc stuff is tiny compared to the real estate and investment accounts anyway." . . .


Ok, this seems reasonable. And if the value is so inconsequential then no reason to account for it in the division.

"My investment accounts are easy to split but here is where I am conflicted. . . .

So you maybe can understand why my daughter is the best choice for executor and the one who will deal responsibly with disposal of assets. When my son gets out of prison, he certainly will need money since he likely will be unemployable. But he would rather not work anyway which bugs me.

This is where my conflict comes in. Does he deserve an equal slice since he has been so irresponsible? I am not saying I would cut him out but I really don't feel good about an equal slice either. And I do have two grandsons, so they would benefit from my daughter having more assets to eventually leave to them."


You have some conflicting goals and will need to sort your own priorities, but I will still write.

What sort of relationship do your daughter and son have? Close, ok all things considered, not on speaking terms? I ask, because cutting out or even a very uneven split can throw a wrench into their relation that makes it much worse or even ends it.

That said, you also seem to be most interested in keeping the wealth in the family, you mentioned your two grandchildren by D but did not mention any by S. Whatever you initially decide, you should think about what you would like to happen if your son has a child or children after you prepare your documents. If you are alive and of sound mind, you can always change them but if you are alive and not of sound mind, will current you be happy with the result? And it is potentially an issue for you because men do not experience menopause; absent unusual circumstances men can become fathers at a much older age than women. I know you know that, but may want to consider if you contemplate direct bequests to the grandchildren.

Also, how do you contemplate the split if the non-real estate assets appreciate more than the land? Other than specific requests, the drafter is likely to use percentages. Look at your example - " My investment accounts are easy to split but here is where I am conflicted. Let’s say my land is worth $1.5M and I have $2.0M in investments at the time I die. So I could make the estate a more or less even split by leaving my son $1.75M in investments and my daughter $1.5M in real estate and $250K in investments, they both get more or less $1.75M that way."

I suspect that this would be written as land to D, and investments 7/8 to S and 1/8 to daughter. What if before your death land becomes worth $2M but investment rise to $3M? D receives $2M in land and $375k in investments and S get $2.625M in investments.

You probably do not want to amend your will every year. And the same competency concern I noted earlier still arises. Unless your will includes some appraisal process for the land and adjusts the split of investments based on the value of the land as appraised, you probably will not be an "equal" split (even ignoring the personal property of de minimis value).

And it could go the other way if the land becomes much more valuable but your investment portfolio pays for several years of LTC highly assisted living/nursing home c are. Land still rises to $2M but portfolio falls to $1.5M. D inherits land and $187.5K and S inherits $1.3125M in investments.

Depending on the age of your grandchildren you might consider funding 529 accounts for them, FWIW.

To me that D as executor is a good choice; name a back-up or back-ups, too, and not your son. Your plan with respect to your daughter seems pretty reasonable. I would consider a trust for S, with an independent trustee (not your daughter) with very limited ability to invade corpus, with balance after S's demise to his children, if any, alternatively split equally between all your grandchildren, OR further alternative to your D's children is S has no progeny.

In any event you need to speak to a good wills and trust attorney, and possibly a second one if you own land in a state that is not your state of residence.

Also, one last thought - do you think that parental love for children should be unconditional or is it acceptable for the parents to condition their love? My sense is that most people who inherit from parents ending up viewing the distribution ratio as a measure of parental love (whether rightly or wrongly). When you write "[d]oes he deserve an equal slice since he has been so irresponsible?" it makes me think that you believe parental love is conditional (whether you do or not). Is that the message you want to send, especially because you will no longer be around to speak or clarify your intent, and leave your D to pick-up the pieces and deal with your S (her brother)?

Good luck,

JAFO

Disclaimer

Yes, I am a lawyer, BUT THIS IS NOT LEGAL ADVICE; it is only general information. NO CLIENT RELATIONSHIP IS INTENDED TO BE CREATED, NOR IS ANY SUCH RELATIONSHIP SO CREATED. FOR SPECIFIC LEGAL ADVICE YOU SHOULD TALK TO A LAWYER IN YOUR AREA.

PS - Apologies for the long post.
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Hi bhm, we all have dirty laundry,aka dysfunctional families,so you’re not alone.

I’m single, lots of assets like you and the way I set up my will is that when I pass, all assets are to be sold. From that, I’ve allocated percentages to be given to various charities. Also, a small amount to my brother so he can’t claim I cut him out of my will, and an amount to my 3 nephews, and 1 niece. The bulk of my estate goes to charity.

My lawyer is my executor and if he passes, someone from the same firm will handle it.

If I had children, I’d leave it 50-50 but set up a trust for the problem child with a lawyer handling it, otherwise, a family member has to handle all the angst of dealing with problem child.

We’re all getting older and I have some assets that need to be sold, such as coins, silver, a few guns, ham radio equipment, a few other unique items, oh and scrap metals. I plan on investing the proceeds.

One thing I remember my father telling me before he died was that although I was more responsible one, he felt it fair to split his estate 50-50. At the time, I didn’t like it but I’ve come to appreciate it.

Hugs, Lucky Dog
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On the other hand, you'll be gone and why should you care how he spends it? It's his life... - Wyomingtim

------------------------

True, but in the period between setting up my estate plan and the time I die, I will have the knowledge that I passed up a lot of things in life that I would have enjoyed with the result being him p..sing it away. In other words, if I wanted it pissed away, I would have done it myself. I would have that to think about for the next fifteen or twenty tears.


There is no need to pass up anything. The estate plan is just that, a plan. It doesn't require that you relinquish control over your assets now, only what will happen to them upon certain event(s). You can deplete all your assets now if you wish. You can become a recluse and supreme LBYMer if you wish.

Those choices remain yours and yours alone.

Ira
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I haven't read all the replies yet, but since you're soliciting input I'll just give mine now. I suspect others may have said similar things.

This is where my conflict comes in. Does he deserve an equal slice since he has been so irresponsible? I am not saying I would cut him out but I really don't feel good about an equal slice either.

That is up to you. It's a family thing. I get the feeling you're a "take responsibility for yourself" kind of guy. Though he is your son, he is making his choices (and dealing with the consequences). Whatever you decide, if he's a lawyer then you want to have an air-tight trust drawn up. You said you had a trust, but be sure it's bullet-proof. So he has no recourse; no basis for which to challenge your daughter's authority. Do you think if he feels slighted he could harm your daughter or grandkids? That's another problem, potentially. Definitely talk to a lawyer.

Maybe give him a "fresh start" slice, i.e. enough to try to get his life back on track but not enough for lifetime largesse (which I get the feeling you're not comfortable with him doing).

If it were me (I only have 1 kid, so I'm projecting a bit here), I would give the daughter almost everything, for her benefit and that of your grandkids. Maybe give the son $250K "to be used to start a business, or such endeavor as to restart your life".

Just my first pass at this. As I read the thread I might think of something else. We structured our trust so that 1poorkid eventually gets everything (duh), but additionally that only her heirs (should she have any) could touch it. Any husband(s) would have no claim ever.

Which reminds me, we probably need to refresh the trust. Should call a trust lawyer. We set it up when she was a minor, and she's now almost 26. So a lot of provisions are no longer relevant.

1poorguy
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OK, I've read the thread. First, I agree with the poster that says you can have a good ole time with your money NOW, rather than have it frittered away by someone else after you're gone. FWIW, I always told my mom that I didn't want her money. She should spend it on herself. Alas, she didn't spend much, which I guess was good because now she needs an AL facility (and they're expensive).

I disagree with the notion of "deserve". No one deserves any of your money, other than entities whom you owe debts (mortgage, taxes, whatever). It's YOUR money, to be doled-out how you see fit. So, IMHO, neither son nor daughter deserve it. It's whatever you choose to give them in alignment with your goals and philosophies. As others said, you could just liquidate the whole thing and give it to Save the Whales if you wanted. Start a foundation. Whatever you like.

But I do agree that you have to consider family dynamics. Is the son on good terms with the daughter? Estranged? Potentially violent? Do you see compelling the son to do something with his life as a greater act of love than feeding his largesse? I won't debate the merits of either position, just laying it out.

In the end, it is up to you and your priorities. Whatever you decide, get a trust attorney and make it air-tight. I hadn't thought of putting a separate trust up for the son, administered by a third-party. That certainly would be an option. Make him a trust fund baby: has money, but can't access any of it without permission.

1poorguy
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1poorguy
We structured our trust so that 1poorkid eventually gets everything (duh), but additionally that only her heirs (should she have any) could touch it. Any husband(s) would have no claim ever.

That is very interesting, was it complicated for the trust lawyer or did it seem pretty much a standard (often used) setup?


nag
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In the end, it is up to you and your priorities. Whatever you decide, get a trust attorney and make it air-tight. I hadn't thought of putting a separate trust up for the son, administered by a third-party. That certainly would be an option. Make him a trust fund baby: has money, but can't access any of it without permission.

If it were me in this situation, (and knowing how hard it is to raise kids it could easily have been me,) I would absolutely go the two trust route. Let son have income sent to him with capital gains staying in trust and increasing value, managed by someone not his sister. This will not be cheap.

The income from the trust can be considerable depending on how it's invested. Have specified goals for him to meet, (staying out of prison for X years, employment for Y years, saving for retirement, whatever gives you comfort,) and give him access to some of the principal as he meets these criteria. It can take as long as you feel necessary. If he does not reach the goals by the time he dies, have alternate recipient in mind.

You can have a consultation with an estate lawyer to go over your options and find out about how much it should cost to put together. This was free for us.

So not easy. Good luck.

IP
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Mike, I don't have any "advice" for you. I just wanted to say that I've had to grapple with some of the same kinds of complications, and I feel for you.

You and I have differed on political stuff from time to time. Your honest, courageous post reminds me how unimportant such stuff can be in the scheme of things. I suspect that many of us would enjoy each other's company over a beer despite (or maybe even because of) such differences.

Take care, brother.
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Beyond the Grave, Revised and Updated Edition: The Right Way and the Wrong Way of Leaving Money to Your Children (and Others) https://smile.amazon.com/dp/0062336223/ref=cm_sw_r_cp_api_gl...

Great book on estate planning written by father/son lawyers with decades of experience. It’s just stories of things gone right and things gone wrong that they’ve seen.

One point they make is that if there is an uneven split between siblings it can cause a permanent rift and lead the lesser sibling to hound their better inherited siblings for “their share”.
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I second StockGoddess's recommendation to read "Beyond the Grave."

A couple of responses encouraged you to spend the money instead of leaving it for disbursement.

Mom and dad did that by gifting funds to my sister and me. Bought me a truck one year and something of equal value for my sister. Consider annual gifts to your daughter and son. Maybe open investment accounts or 529s for the grandkids. Make the gifts equal and see how it is spent. Or, a long weekend family get together somewhere. A friend used to take his entire extended family (10 total) to Hawaii for a week and pay for the whole thing. Great for memories and spending time together.

None of this requires a trust or anything complicated - just parting with some of your funds. Start small and see how it goes.

PW
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It was fairly easy. We just specified 1poorkid, and then her descendants. If they aren't named, they have no claim (as best I understand). Obviously this could vary by state. But our guy seemed to think it wasn't a problem organizing like that.

1poorguy
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"It was fairly easy. We just specified 1poorkid, and then her descendants."

Dad did the same thing. That's why I disbursed directly to my middle brother's 4 sons rather than his wife.

We still have a good relationship with his surviving wife, and we still have beach vacations with her family and ours.

But it was helpful to take her out of the equation when it came to disbursing Mom and Dad's estate.

No room for debate or discussion or acrimony.

FWIW, Dad was the Commissioner of Accounts in our home county and had an estate planning practice.
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If it were me (I only have 1 kid, so I'm projecting a bit here), I would give the daughter almost everything, for her benefit and that of your grandkids. Maybe give the son $250K "to be used to start a business, or such endeavor as to restart your life". - 1PG

---------------

I have thought something like this could be part of it. He is more or less unemployable and like I said is not inclined to work anyway. So I could provide him a monthly stipend to keep a roof over his head while I am still living. This is done with the understanding he is getting some of his inheritance early. Unfortunately, this still leads to a disproportionate distribution when I die. Or worse if I do an equal split at my death, then the monthly stipend actually served to increase my sons take to be greater than his sister.

I guess I am still hung up, maybe unfairly, on the idea that his lack of a work ethic should not be rewarded, especially by me placing myself in the role of being an enabler.
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Mike, I don't have any "advice" for you. I just wanted to say that I've had to grapple with some of the same kinds of complications, and I feel for you.

You and I have differed on political stuff from time to time. Your honest, courageous post reminds me how unimportant such stuff can be in the scheme of things. I suspect that many of us would enjoy each other's company over a beer despite (or maybe even because of) such differences.

Take care, brother.

------------

Thank you Mister Fungi for your touching sentiment, really.
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One point they make is that if there is an uneven split between siblings it can cause a permanent rift and lead the lesser sibling to hound their better inherited siblings for “their share”. - StockGoddess

--------------------

My son and daughter already have a strained relationship more-or-less for the same reason as my angst. Initially they were close but when he quick working and adopted his ner-do-well lifestyle when meanwhile she was working her azz off along with raising two kids, she lost a lot of respect and tolerance for him.

And as she and her husband got more and more ahead, while he was living in an RV, I think deep down he resented her success. Him going to prison was sort of a final straw as far as she is concerned. I am not a shrink so who knows the root causes but one thing for sure, they are not close. Maybe that rift will heal some day, I wish it would, but it is out of my hands, but I do want to avoid throwing fuel on that fire if I can.
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"I guess I am still hung up, maybe unfairly, on the idea that his lack of a work ethic should not be rewarded, especially by me placing myself in the role of being an enabler. "


********************************************************************************

An inheritance is a transfer of funds - not a reward for the inheritor.
Your will simply states what you want to do.

Howie52
What you want to do is the only thing that matters in this instance. Children are who and what
they are and while people of all and any stripe can change - inheriting money would rarely be
the cause of a change.

Good luck.
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Or worse if I do an equal split at my death, then the monthly stipend actually served to increase my sons take to be greater than his sister.

I guess I am still hung up, maybe unfairly, on the idea that his lack of a work ethic should not be rewarded, especially by me placing myself in the role of being an enabler.


Have you talked to your daughter about this? I had an older brother who had disabling mental issues. I told Dad more than once to give my share of the estate to Bro, which he still did not do. Talk to your daughter and see how she feels about things, rather than assuming what she would feel.

IP
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So I could provide him a monthly stipend to keep a roof over his head while I am still living. This is done with the understanding he is getting some of his inheritance early. Unfortunately, this still leads to a disproportionate distribution when I die. Or worse if I do an equal split at my death, then the monthly stipend actually served to increase my sons take to be greater than his sister.

this particular part is easy to fix. if you provide a monthly stipend to your son, provide one as well for your daughter.

c.
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Mom and dad did that by gifting funds to my sister and me. Bought me a truck one year and something of equal value for my sister. Consider annual gifts to your daughter and son. Maybe open investment accounts or 529s for the grandkids. - nothingissimple

I have sort of been doing that by funding the annual Roth contribution for both my daughter and her husband. I would do the same for my son, but you have to have earned income which is anathema to him. I can think of more things like that to do, but in the end, I still will have my estate paradox.



Make the gifts equal and see how it is spent. Or, a long weekend family get together somewhere. A friend used to take his entire extended family (10 total) to Hawaii for a week and pay for the whole thing. Great for memories and spending time together.

None of this requires a trust or anything complicated - just parting with some of your funds. Start small and see how it goes.

PW


Good thoughts but I suffer from a problem that has been discussed on the board before, after a lifetime of saving, switching over to a more free-spending mode in retirement. I am quite happy with my simple and inexpensive lifestyle.
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Have you talked to your daughter about this? I had an older brother who had disabling mental issues. I told Dad more than once to give my share of the estate to Bro, which he still did not do. Talk to your daughter and see how she feels about things, rather than assuming what she would feel.

IP


-------------

Excellent advice. I have talked to her about generalities concerning my estate but haven't gone into the issues I have brought up on this board. She may very well have some important perspective that hasn't occurred to me or at least will have a chance to express any concern she has with some of the ideas I already had or the news ones suggested by the board.

Thanks.
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Random thoughts:

My parents split their estate in four equal parts, minus the funding of a scholarship in my Dad’s name to the college he attended that got him out of a laborer’s life in South Dakota. So - no dissension. That said, he had a quite specific conversation with me (and I presume the other three kids) about it, and more than that left behind a three ring binder with thoughts and reasons for his decisions, to be instructive for his executor (my sister) should there be any confusion. There were several pages, and I presume they were not “legal” in the binding sense, but could give direction to a judge or other legal entity which might become involved for whatever reason

My parents will also began with a statement to the effect: “These are our sentiments and directions for the disposal of our estate. Anyone who challenges any part of this should be immediately and completely disinherited and the remainder equally divided among the others.” I have no idea if that is legally binding, but it surely would give you pause to complain about it. (There was dissension when my Grandmother on my mother’s side passed, so perhaps that is why the clause was in there.)

As we have no children our will directs any surplus (after taxes) to various charities which are named in the will. However rather than having to update the will frequently, we are permitted to change the list of charities and attach it with only a notarized letter, which cuts down on lawyer fees.

We have also added a modest payment to each sibling (to insure that, as some legal minds might argue “they were forgotten”), but there is a larger trust established for one sister who is a good soul, has a good heart, but has barely two nickels to rub together. We tried to figure out a way to establish it with regular (modest) payments so that the JG Wentworth’s of the world can’t convince her to “cash out”, but our lawyer said that’s almost impossible to achieve so we’ve left it at that. Hopefully she will take the income stream and add it to her modest SS payments. She is a good person but had little success in her field (education), but is more inclined to give her money to someone “who needs it more” even though she lives in a trailer and drives a 15 year old car. All the other siblings have had career success and/or pensions and the like, so no one dies in poverty.

My father directed payments to each of us four children almost annually during the final decade of his life, $13,000 per year was the maximum permitted at the time I think, and each one came with a handwritten card. One year it said “The stock market has been good to me this year, so here is something to enjoy along with me. Don’t get used to it every year, the market isn’t always so pleasant.” Another time he said “I love this country and I pay my taxes, but here is a present that will help me keep my portfolio a bit less within the taxman’s reach…” I don’t know if that was true, it was so long ago.

We have a “professional” executor who gets a percentage of the estate, if/when it is liquidated. They get paid nothing until then. We are old enough that our siblings are likewise old and could predecease us, and we don’t know any of the nieces and nephews well enough and they would all have conflicts of interest, wouldn’t they?

Mrs. Goofy and I have a trust. What a PITA. Once. Haven’t though about it again in 10 years.

I guess that’s enough to add for a while; good luck with your mission.
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A side question for Mr. Goofy, should he return to the conversation. It relates to:

However rather than having to update the will frequently, we are permitted to change the list of charities...

Under what circumstances would you change your list of charities? I'm imagining when a new one comes into view or an older one seems to have lost its focus, but I don't wish to presume.

Pete
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bighairymike:

{{{Mom and dad did that by gifting funds to my sister and me. Bought me a truck one year and something of equal value for my sister. Consider annual gifts to your daughter and son. Maybe open investment accounts or 529s for the grandkids. - nothingissimple}}}

"I have sort of been doing that by funding the annual Roth contribution for both my daughter and her husband. I would do the same for my son, but you have to have earned income which is anathema to him. I can think of more things like that to do, but in the end, I still will have my estate paradox."

Interesting. You also previously wrote: " So I could provide him a monthly stipend to keep a roof over his head while I am still living. This is done with the understanding he is getting some of his inheritance early. Unfortunately, this still leads to a disproportionate distribution when I die. Or worse if I do an equal split at my death, then the monthly stipend actually served to increase my sons take to be greater than his sister."

You do not seem to be worried that $12,000/year to D and Son-inlaw do not create an unequal distribution favoring D over S.

Seems to me that a $1,000 monthly stipend to son would actually even the scales rather than being disproportionate as you first wrote.

It is your money and you can do as you wish but you seem to be very conflicted.

I also like the the idea of spending money currently taking "experiences" especially once S is free.

Also why do you consider letting descendants receive your estate as rewarding behavior in stead of celebrating/rewarding familial relationship? If you really believe that equal distribution rewards your S for "his lack of a work ethic" then it follows that you want to punish him for the same lack of work ethic. This is atypical for me, but you might want to speak to someone so you can clarify your own thinking, and once clearer, I expect that you will be less troubled in making your decisions.

Good luck.

Regards, JAFO
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... unemployable ... a monthly stipend to keep a roof over his head...enabler.

By most estimates, there are over 500k homeless people in the US, so your concern is valid and understandable.

When my brother was in prison, his plan was to go live with his girlfriend. A couple of years before his release date, she died, and he didn't really have a Plan B. Given that he barely graduated high school, and his troubles since then, I was pessimistic about his prospects. I sent him info on re-entry programs, and he didn't respond. I donated generously to the homeless shelter near me, so that if he turned up on my doorstep I'd have a place to take him without feeling too guilty about it.

I was willing to pay whatever shelter or program that would take him, without giving him money directly. That was my solution to my dilemma of how to help without enabling. So maybe you could look into ways to help out your son at arm's length?

As it turns out, bro wasn't interested in any shelter or program, but he's doing OK now anyway, over two years post-release. He's been working in construction, a field in high demand with low barriers to entry, and that currently pays well. He's living with his latest girlfriend. Looking to the future, he might still do something stupid that lands him on the street or back in prison, but that would be his choice, and I don't worry about him any more.
Obviously, if he were my son and not a sibling, I would continue to worry, but my ability to control his life would be just as constrained.
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Mrs. Goofy and I have a trust. What a PITA. Once. Haven’t though about it again in 10 years.


Would you kindly elaborate on why you say it's a PITA? The Countess and I have a trust. I don't recall why we set such a thing up. Likely some sweet talking attorney convinced us we needed one. What are the negatives? One possible upside would be that if we both croak in an accident, the executor will disburse our stuff in accordance with the terms of the trust. No will need be probated?

Like you, we have no children. My sister is comfortable and won't need money. Brother could use but doesn't really need money. SIL is a wastrel who will inherit well from her mother, but we fear she will just blow through it.

The Countess went to a Catholic girl's school in a poor part of town and she wants to give them a meaningful amount - some way for a poor girl to go to a school she couldn't otherwise afford. Maybe even a perpetual scholarship fund. [I think she needs to sit with their administrator to discuss how best to accomplish this.] The school is in her will, but the amount needs to be updated to our today's circumstance. Maybe it should be in the trust?

Hmmm. I see that I have rambled. I suppose I am really asking for suggestions on how to plan for the disbursement of the NoCount fortune.

CNC
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What a PITA. Once. Haven’t though about it again in 10 years.
Would you kindly elaborate on why you say it's a PITA?

Not Goofy, but:
My dad's, and DH's and my, trusts were a PITA to set up because although the attorney put the houses into the trusts, it was our job to move all our bank, credit union, and brokerage accounts. And of course each institution has its own forms and procedures.
Once that was all done, no problems at all.
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We have two trusts. We list each other as the primary beneficiary and our trusts as secondary beneficiaries. It took time to make the rounds to update the account beneficiaries for everything, a few months, but it doesn’t need to be done in a day. Our lawyer gave us the exact wording. I’m used to it now when a new account/job comes up.
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It is your money and you can do as you wish but you seem to be very conflicted.

IMO the conflict is about family relationships, current and future, rather than disposition of money.

I think most parents with more than one child go through the angst of the perception of treating one child differently from the other. In reality, there is sometimes a need to do so, but it does not mean you love one less than the other.

We are wrestling with that now. Eldest did beautifully with his entrance into the adult world while Youngest has struggled since middle school with ADHD, depression and anxiety, which has been crippling at times. We currently wrestle with providing him our lower level apartment rent free while he struggles with getting an entry level job in his field during a global pandemic, where the screaming need for employees are for jobs that don't require a college degree. The concern involves the question of are we enabling him, or supporting him? It can be a fine line, (and one I am not looking to discuss here.)

We also had told them our paying for college was their inheritance, which may very well be the total sum of what they get if we don't get taken out by a semi while traveling together on a highway....a much bigger risk in retirement as we are seldom apart. We intend to spend our money if we can, and some of that will be on annual family vacations to try to bring our kids closer together and give them some great family memories. Though they seemed polar opposites to each other as kids, I am glad to say that they seem to be finding common ground lately, and I have hope that they will feel some sort of family connection to each other by the time we pass.

When kids are involved it's almost always about more than dollars and cents.

IP
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In my family parents try to treat their children equally. But reality is they have different needs. So one has to adapt to the circumstances.
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inparadise:

<It is your money and you can do as you wish but you seem to be very conflicted.>

"IMO the conflict is about family relationships, current and future, rather than disposition of money."

I beg to differ. The references to "rewarding" the son who choses not to work (as a lawyer) seem to me to be about the disposition of money.

In fact, I read some of it like the people to poo-poo FIRE (or at least Earl Retirement) because someone is not maximizing lifetime wealth.

We do not know much about OP's son other than he stopped practicing law, traveled in an RV and ended up in jail (but not why, I do not expect OP to explain). If he did some odd jobs and and otherwise paid his bills in order to travel when he was young(ish) as opposed to 60-80 weekly stressful hours to maximize his wealth, so what. What I hear between the lines is resentment regarding S's choices, similar to what is often expressed to those who RE.

"I think most parents with more than one child go through the angst of the perception of treating one child differently from the other. In reality, there is sometimes a need to do so, but it does not mean you love one less than the other."

I do not disagree. I believe I acknowledged as much when I suggested a Trust and income for OP's S and no real concerns for distribution to OP's daugher.

"We are wrestling with that now. Eldest did beautifully with his entrance into the adult world while Youngest has struggled since middle school with ADHD, depression and anxiety, which has been crippling at times. We currently wrestle with providing him our lower level apartment rent free while he struggles with getting an entry level job in his field during a global pandemic, where the screaming need for employees are for jobs that don't require a college degree. The concern involves the question of are we enabling him, or supporting him? It can be a fine line, (and one I am not looking to discuss here.)"

Agreed and enough said.

"When kids are involved it's almost always about more than dollars and cents."

I do not disagree.

I also note that you do much communicating with your two boys. OP seems not to have discussed much or any) of his plans with D or S. And I note that good communication is a fraught process, with multiple places it can go awry. The speaker needs to know what they want to communicate, then the speaker needs to finds the words or way to communicate it, the recipient needs to hear/see the way the speaker chooses to communicate it, and then the recipient needs to decipher the intended message.

And the process can breakdown anywhere along the way. How many times has a speaker said "that is not what I meant" because either the speaker did not express intent clearly or recipient did not understand decipher correctly. Good listeners tend to repeat back in their own words to the speaker so the speaker can confirm the the correct message was communicated.

https://www.mindtools.com/CommSkll/ActiveListening.htm

"Our personal filters, assumptions, judgments, and beliefs can distort what we hear. As a listener, your role is to understand what is being said. This may require you to reflect on what is being said and to ask questions.

-- Reflect on what has been said by paraphrasing. "What I'm hearing is... ," and "Sounds like you are saying... ," are great ways to reflect back.

--Ask questions to clarify certain points. "What do you mean when you say... ." "Is this what you mean?"

--Summarize the speaker's comments periodically.

When all parties are alive feedback and correction is available. A will is not a medium that allows for any confirmation or clarification if the recipient does not understand the intended message. And if it is misunderstood, it often adversely affects the remainign relationship between the remaining family members (or siblings in OP's case).

Just my $0.02.

Regards, JAFO
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IP writes: It is your money and you can do as you wish but you seem to be very conflicted.

IMO the conflict is about family relationships, current and future, rather than disposition of money.


IMO, (might be wrong, might be inaccurate, might be the ramblings of a madman*)... it seems angst based on making VALUE JUDGEMENT about others.

I'm facing a similar set of choices: no kids of my own, so nephews (nieces only by marriage) who rarely interact with me.
Some are "fine, up-standing"... others I find "wanting".

99% of my assets are in brokerage accounts, in which I used the ToD (transfer on death) options, listing the nephews all as equal beneficiaries.

I struggled for a while with the "disapproval/judgemental" thoughts... but after a while I asked myself several questions:
"How would I want to be treated?", (the Golden rule)
"How would I want to NOT be treated?" (Silver rule)
And... "what are MY ethics? (not my morals, and especially not "legal"... what are my ethics?).
"Who am I to judge...?"

Therefore, I settled on an equal split between them all and let each one run his own life.
I've enough trouble running my life.

I really appreciate all the comments in this thread. It makes me re-evaluate my thoughts and choices.

My choice also plays into my attempts to follow Buddhism's 4-Noble Truths, and the 8-Fold Path, and helps me to avoid the angst associated with "judging" my nephews and trying to allocate my resources as influenced by my "attachment" to those resources.

🤔
ralph


*Tom Nash
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This thread has been interesting and has come at an opportune time. My wife died intestate in 2019 several months after her mother died leaving her a significant estate. The California Probate Court assigned me the role of administrator. I named my 3 children as POD beneficiaries on all accounts at banking institutions and as TOD beneficiaries on all brokerage investment and IRA accounts.

I recently realized that this presented a problem with how to deal with debts and taxes in the year that I died. All the wealth would have been transferred to the beneficiaries. I have scheduled a meeting with a law firm that does estate planning in December.

One question that I have is does it make sense to have a trust as a beneficiary of an IRA instead of using a TOD? The only function(s) that need to occur are splitting the IRA into three equal parts and are titled as Inherited IRA for each beneficiary?
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"One question that I have is does it make sense to have a trust as a beneficiary of an IRA instead of using a TOD? The only function(s) that need to occur are splitting the IRA into three equal parts and are titled as Inherited IRA for each beneficiary? "

It would seem to be NO.

IRAs are INDIVIDUAL Retirement accounts.

Upon death of the owner of the IRA, it needs to go to a beneficiary directly.

Normally, for a wife, it would pass to husband without written instructions. as a spouse.

Any other split will result in the 'heirs' having INDIVIDUAL retirement accounts which they will have to quickly spend down to ZERO.

IF the are younger than 72

" If the owner was younger than 72,* the assets must be completely distributed by December 31 of the 5th year containing the anniversary of the IRA owner's death."

https://www.fidelity.com/building-savings/learn-about-iras/i....

The IRS wants its money.

You can't dole out an IRA over 20 years if you are under 72 when you get it. Five years.

For a younger non-spouse 'inheritor', a boat load of taxes will be paid over those 5 years.

t.
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Any other split will result in the 'heirs' having INDIVIDUAL retirement accounts which they will have to quickly spend down to ZERO.

IF the are younger than 72

" If the owner was younger than 72,* the assets must be completely distributed by December 31 of the 5th year containing the anniversary of the IRA owner's death."

https://www.fidelity.com/building-savings/learn-about-iras/i.......


This is specifically for trusts, charities and estates - not for non-spousal beneficiaries like children.

You can't dole out an IRA over 20 years if you are under 72 when you get it. Five years.

For a younger non-spouse 'inheritor', a boat load of taxes will be paid over those 5 years.


Nope. 10 years, not 5. From your same link, on the "non-spouse" tab:

If the original account owner died on or after January 1, 2020, in most cases you will need to fully distribute your account within 10 years following the death of the original owner. However, there are exceptions if you are considered an eligible designated beneficiary. Eligible designated beneficiaries include a minor child of the original account owner, a disabled or chronically ill individual, or any other person who is not more than 10 years younger than the deceased account holder. If you are an eligible designated beneficiary, you can still withdraw RMDs based on your age.

AJ
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One question that I have is does it make sense to have a trust as a beneficiary of an IRA instead of using a TOD? The only function(s) that need to occur are splitting the IRA into three equal parts and are titled as Inherited IRA for each beneficiary?

Probably not, but ignore Tele's reasoning (or lack thereof). The real reason is that a trust would only have 5 years to completely disburse the account, and if the trust is paying the taxes, it will be taxed at the generally higher trust rates. If your kids split get it through a TOD, rather than the trust, they will each have 10 years to fully disburse their account, so they can figure out how to do it best for their own tax impacts.

Having just gone through splitting up an IRA that was inherited by children, I can say that it's not that hard to do. One of the beneficiaries just has to call the administrator (broker) and let them know that the owner has died. The administrator will request a copy of the death certificate. I was able to e-mail a PDF of the death certificate to the administrator. Then each beneficiary has to contact the administrator to get the IRA transferred to an inherited IRA - either at the current broker, or they can have it transferred to a brokerage of their choice.

AJ
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From Fidelity:

"IRA assets must be distributed within 10 years if the trust is structured as a conduit trust and the current beneficiaries are the surviving spouse and non-EDB children, or if the trust is structured as an accumulation trust9. But if the trustee retains assets in the trust, this may result in adverse tax implications."
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The concern involves the question of are we enabling him, or supporting him? It can be a fine line, (and one I am not looking to discuss here.) - inparadise

I don't see it as a fine line. When the recipient through no fault of their own is struggling but really trying to fulfill their potential, then whatever support you provide is just being a loving caring nurturing parent. Enabling, in my mind anyway, involves facilitating a negative situation brought on through fault of their own.

In the case of my son, he is very intelligent, but not highly motivated as far as working is concerned. When he was in high school, he had the usual string of unskilled jobs and was far from a reliable, eager employee. He went through a lot of different jobs with long spans of not working at all. Basically he was a low performing marginal employee.

After he got his BS degree, he worked for year and then decided he wanted to go to law school. Five years later he graduates and passes the bar and starts a good career with a law firm in Florida. I was proud of my son the lawyer and his career was going well. He did have to work long hours but was well paid for it. He complained that he just did not have enough free time to do the things he really enjoyed which primarily was going to live music concerts, lots of them, I am talking hundreds going back to include his HS days. After about three years, he just up and quit his attorney job, and started living in an RV and just traveled around the country camping and going to rock concerts and music festivals.

I worked steadily for 45 years and always had to balance my career with fitting my vacations in as best I could around the priorities of the job. And my daughter and her husband are both working very hard and being responsible adults raising two kids and have a lot to show for it.

My son on the other hand just wants to coast through life, with little or no responsibility, still acting like a perpetual college student but without any classes to interfere with partying. He could and did hold down a good job and simply decided not to work. It is that lack of a work ethic that I don't feel good about enabling.

Anyway, providing support is being a responsible parent, enabling a lazy persons desire to bum around is something quite different.
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Aside from the technical points AJ made, I have an issue with this:

Any other split will result in the 'heirs' having INDIVIDUAL retirement accounts which they will have to quickly spend down to ZERO.

Not spend, but withdraw. I can be a picky SOB about wording, but I don't see this as being picky. While the beneficiary might spend any or all of it, and in the case of a traditional IRA they at least have to cover the taxes, investing rather than spending should always be a consideration. This is, after all the Retirement Investing board.
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telegraph:

"One question that I have is does it make sense to have a trust as a beneficiary of an IRA instead of using a TOD? The only function(s) that need to occur are splitting the IRA into three equal parts and are titled as Inherited IRA for each beneficiary? "

"It would seem to be NO." I believe that this is generally correct.

"Normally, for a wife, it would pass to husband without written instructions. as a spouse.

Any other split will result in the 'heirs' having INDIVIDUAL retirement accounts which they will have to quickly spend down to ZERO."


10 years is not exactly quickly. And the heir does not need to spend it, it needs to be withdrawn for the IRA.

"" If the owner was younger than 72,* the assets must be completely distributed by December 31 of the 5th year containing the anniversary of the IRA owner's death."

https://www.fidelity.com/building-savings/learn-about-iras/i...


That is the old rule and no longer in effect. When the 5-year rule was in effect, the "Stretch" rule provisions were also available, but those stretch rules are gone now, since the 10-year rule and age 72 rule (instead of 70 1/2) were put place.

Also, if the beneficiary has other income and is not otherwise maxing 401k and IRA, the inherited IRA can be used to subsidize current lifestyle while increasing IRA and 401k contributions to the max. Money is essentially fungible.

Regards, JAFO
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bighairymike: "My son on the other hand just wants to coast through life, with little or no responsibility, still acting like a perpetual college student but without any classes to interfere with partying. He could and did hold down a good job and simply decided not to work. It is that lack of a work ethic that I don't feel good about enabling."

If he is paying his bills and not hitting up family and friends for money, why does it bother you so much?

Do think the same about people who retire early?

Using an obvious TMF example, do you believe that intercst and his apparent lack of traditional work ethic is problematic?

If not what is the difference?

"Puritanism: The haunting fear that someone, somewhere, may be happy.” H.L. Mencken

Regards, JAFO
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"Not spend, but withdraw. I can be a picky SOB about wording, but I don't see this as being picky. While the beneficiary might spend any or all of it, and in the case of a traditional IRA they at least have to cover the taxes, investing rather than spending should always be a consideration. This is, after all the Retirement Investing board."

I have a feeling that this board is comprised of people who started with nil decades ago and had no background in investing when we started out 20, 30, 40 years (or more) ago. So many of us are or were blundering about in the dark trying to teach ourselves how to invest while we were approaching, nearing or in retirement. That is why we are here. We did not come from wealth and we are teaching ourselves how to manage wealth late in life.

Many of us really don't know what to do with our money now that we have more than we really need.

Most of us got here by learning to enjoy life without spending every last nickel and our needs are few. That will not change for most of us.

We've sort of 'won the game' but 'what now?' Keep going like we're going and die feeling like our life was a game of Monopoly? Get serious about charitable donations that we talked about but did not seriously support along the way? Help our grown children/grandchildren without enabling them (whatever that means)?

As for RMD's, your point is well taken. If you don't even need your RMD's to live on, why are we obsessing over the taxes? We can avoid some taxes by giving or increasing our giving the RMD's to charities we previously supported. We can make $15,000 gifts (or whatever the number is nowadays) to our children and/or grandchildren. We can put those gifts in college funds if we don't want to make unrestricted gifts. We can take our RMD's and our SS checks and invest them in taxable accounts if we want, and treat the ever increasing dividend and interest income as pay raises.

What to do with wayward children?

That is a personal choice that varies with the individual.

I personally would lean in the direction treating them equally unless they are at risk of harming themselves - i.e., drug or alcohol addictions.

That way you eliminate the additional hard feelings that come with unequal treatment.

But it is a personal choice.
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Using an obvious TMF example, do you believe that intercst and his apparent lack of traditional work ethic is problematic?

If not what is the difference? - JAFO


---------------------

Intercst earned his retirement nestegg on his own, LBYM coupled with savvy investing. He did not have his wealth handed to him, and he does not rely on ongoing subsidies (Obamacare aside) of his chosen life style.

That is a considerable difference.
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I'm facing a similar set of choices: no kids of my own, so nephews (nieces only by marriage) who rarely interact with me.
Some are "fine, up-standing"... others I find "wanting".
...
I struggled for a while with the "disapproval/judgemental" thoughts... but after a while I asked myself several questions...


I don't have a good answer to the questions about how to disburse assets in a will. But, maybe a partial solution is to get rid of some assets while you're alive. Is one of the things you want to subsidize that your niece/nephew attends college (or trade school, or something else)? You could give 'em a scholarship. You want to assist one in trading an unreliable car for a better one? You could give some "matching money."

If you're worried about perception of inequality/unfairness after you pass away, this is outside that. That is, these things were "sort of" available to any of them earlier, but they didn't make the choices to get them.

This may not apply to everyone, especially if you have the level of assets where you can't afford to give some away now. But for some early retirees, you have to be tighter with your assets before drawing Social Security when you self-fund 100% of your needs and account for poor market returns, and then at (say) 70, you have SS income stream and there aren't as many years of portfolio variability ahead.

As always, just a suggestion to apply or not, or modify as you see fit.
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Not spend, but withdraw. I can be a picky SOB about wording, but I don't see this as being picky. While the beneficiary might spend any or all of it, and in the case of a traditional IRA they at least have to cover the taxes, investing rather than spending should always be a consideration. This is, after all the Retirement Investing board.

1. Agree with the clarification on the wording.

2. I intend to use the mandatory withdrawals of inherited Roth IRAs to fund the taxes on IRA to Roth conversions, so kind of "investing," and kind of something else (but related).

3. Also, not counting on any inheritance or that the timing would be to my preference...although the longer it takes to get any inheritance means those people are around that much longer.
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"How would I want to be treated?", (the Golden rule)
"How would I want to NOT be treated?" (Silver rule)


Nassim Taleb referred to that second one as "the Platinum Rule" (don't treat others as you wouldn't want to be treated) because the "not doing" is more important than the "doing" of the Golden Rule. An odd distinction, but I've been seeing the wisdom in it over the last several years.
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So if you divide the estate equally, who are you really helping if the son is going to blow through it?

I had a cousin who had settlement of $450,000 given to her when she turned 25. This was in the mid 1980's. I'm not sure of the details other than the money came from death of her mother from a car crash when she was an infant. Her mother's parents also left her mother's portion of their estate to her too.

Anyway, Sherry quit her job when she received the money, went on trips, bought boats and other big ticket items. She also had a recreational drug use problem. Within 2 years she was broke and back to working.

So who benefited? The boat dealer, the travel destinations, and others.

I guess she has the memories.

gcr
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bighairymike:

<<<Using an obvious TMF example, do you believe that intercst and his apparent lack of traditional work ethic is problematic?

If not what is the difference? - JAFO>>>

---------------------

"Intercst earned his retirement nestegg on his own, LBYM coupled with savvy investing. He did not have his wealth handed to him, and he does not rely on ongoing subsidies (Obamacare aside) of his chosen life style.

That is a considerable difference."


You know your family situation better than I do, and I understand not wanting to post details on a public board, but you have never given any indication that your S was not covering his own expenses, meager as they might have been, without hitting you or his S or other family up for money.

If he was happy living a simple lifestyle, living in an RV, traveling around the country, and paying his own bills, why does it bother you so much?

I cannot tell whether you believe that everyone is obligated to maximize potential earnings, toiling away at work until age 65(or 67), whether you are envious of the choices he made that you did not, or whether the situation embarrasses you because you cannot brag about your lawyer son when speaking to your peers.

Obamacare is a pretty big subsidy. IIRC, intercst believes it is in the range of more than $1,000 month compared to what he expected to be paying.

Are you familiar with the Travis McGee retirement plan - "a beach bum who subscribed to his own peculiar philosophy that retirement [sh]ould be taken not all at the end as an old man but as early and as often as fortune allowed. In short, our days are numbered and not to be wasted battering away at some tedious task for damned fools. It’s not a prosperous life but you get to spend a lot of time in the sun."

John D, McDonald speaking through Travis McGee: "I take my retirement in installments, whenever I can afford it."

See also, Tim Ferriss’ The 4-Hour Workweek and the financially independent, retire early (FIRE) movement. Ferriss refers to the mini retirement. He suggests developing efficiencies in our life and put systems into place so one drop out of the rat race for weeks, maybe even months at a time, before returning to regular life to continue where we left off. Retirement is for now, not tomorrow. Why waste the best years of our lives in pursuit of a retirement when we are old and feeble?

Not a lifestyle for everyone, probably, but not necessarily wrong either.

Regards, JAFO
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Anyway, providing support is being a responsible parent, enabling a lazy persons desire to bum around is something quite different.

Then I think you answered your own question. I agree with the suggestion regarding talking to your daughter, especially since she will be the administrator and have to deal with him.

You might also give your son a "heads-up" that this is what you're going to do unless he changes his ways (which he probably won't).

1poorguy
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I don't see it as a fine line. When the recipient through no fault of their own is struggling but really trying to fulfill their potential, then whatever support you provide is just being a loving caring nurturing parent. Enabling, in my mind anyway, involves facilitating a negative situation brought on through fault of their own.

I don't disagree, however, you don't have the full picture with our situation and I am not going to discuss it here.

So very many shades of gray, no black and white. Absolute refusal to share information makes it tough to determine "really trying." At least we know he is safe if he is downstairs. Dealing with anxiety and depression is not simple. Don't nudge and risk them setting bad habbits. Nudge and risk their going off the deep end. Damned if you do, damned if you don't, so we just focus on letting him know he is loved and we are here if he needs us.

IP
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...why does it bother you so much?

FWIW, I'm avoiding making any value judgments. The fact is, it does bother him. And it's his estate to leave to whomever he chooses. Notice in the subject heading the use of the word "angst". So, to be fair to him, it does bother him. In fact, it bothers him in TWO ways. First, enabling what he considers irresponsible behavior. And, second, unequal disbursement because he still loves his son despite everything that has happened (or at least, it sounds like that is the case).

It sounds to me like this is the "Goofus/Gallant" psychology conflict.

Plus we don't know why he was in prison. Drug use? Assault? Murder? We have no idea (and it's none of our business). If it were me, the reason for the imprisonment would affect my attitude. If he was in for rape? I wouldn't leave him a dime (for example).

I don't think there is a right/wrong answer. It's just right or wrong for him, and it seems both options are right AND wrong, hence the "angst".

I'm just being a sounding board. Giving options. Not trying to make value judgments for him because I think his values are different than mine.
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What are "non-EDB children"?

How does one attach a TOD to an IRA? [And can this sort of thing be done with a 401(k)]? I thought that all we could really do with an IRA was to name beneficiaries -- and even then, as I understand it, a spouse can override the named beneficiaries.

culcha
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1poorguy:

<<<... why does it bother you so much?>>>

FWIW, I'm avoiding making any value judgments."

I believe that I have been very respectful of OP, have asked may open ended questions, and am well aware that this is a public board that most people do not necessarily want to air all personal details

"The fact is, it does bother him."

It does. But I think understanding why it bothers him might aid in devising a solution with which he is comfortable. The unexamined life and living and why.

"And it's his estate to leave to whomever he chooses."

I do not disagree and have acknowledged that several times.

"Notice in the subject heading the use of the word "angst". So, to be fair to him, it does bother him."

Agreed.

"In fact, it bothers him in TWO ways. First, enabling what he considers irresponsible behavior. And, second, unequal disbursement because he still loves his son despite everything that has happened (or at least, it sounds like that is the case)."

Or perhaps more ways than that. I believe the angst will continue until he understands why it bothers him.

"Plus we don't know why he was in prison. Drug use? Assault? Murder? We have no idea (and it's none of our business). If it were me, the reason for the imprisonment would affect my attitude. If he was in for rape? I wouldn't leave him a dime (for example)."

Agreed, generally, but he did write "[t]hen he got in trouble with the law for reasons that are too embarrassing to talk about, but not murder or anything like that, . . . ." so I assume it is not rape for that would likely be more than mere embarrassment.

"I don't think there is a right/wrong answer."

Agreed.

"It's just right or wrong for him, and it seems both options are right AND wrong, hence the "angst"."

Which leads back to my questions. If he really understood why he was so "angsty" it would probably be easier for him to resolve with inner peace with his decision, whatever it might be.

"I'm just being a sounding board. Giving options. Not trying to make value judgments for him because I think his values are different than mine."

I do not believe that I have been doing anything different. My questions were all directed to lead to self-reflection and to make him think why and the potential consequences of his different options.

Regards, JAFO
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I believe that I have been very respectful of OP, ...

Sorry, didn't mean to imply otherwise.

Or perhaps more ways than that. I believe the angst will continue until he understands why it bothers him.

Fair enough. Or maybe he already understands it, but can't shake it. Like a fundy Xian who finds out the son is gay. With every fiber of their being they believe it is sinful, yet it is their son. Some disown them, some live in denial, some change their views (I believe Dick Cheney did the latter).

...so I assume it is not rape for that would likely be more than mere embarrassment.

Good point. Maybe it was just illegal campfires in national forest. But "not murder or anything like that", while vague, does eliminate a lot of stuff.

My questions were all directed to lead to self-reflection and to make him think why and the potential consequences of his different options.

Ah. Self-reflection is generally a good thing. I strongly suspect we have a Goofus (son) vs Gallant (hairymike) situation. There is a lot of psychology involved there.

It will be interesting to see what he ends up doing (should he choose to share it with us).

1poorguy
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bighairymike writes,

Intercst earned his retirement nestegg on his own, LBYM coupled with savvy investing. He did not have his wealth handed to him, and he does not rely on ongoing subsidies (Obamacare aside) of his chosen life style.

That is a considerable difference.

</snip>


Actually the benefit I get from the lack of taxation on unrealized investment gains is far greater than any Obamacare subsidy. You guys really need to understand the tax code. Working for wage & salary income is just about the dumbest thing you can do, taxwise. I'm glad I learned that at a relatively young age (about 35).

intercst
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What are "non-EDB(sic) children"?

EBD is Emotional and Behavioral Disorder

How does one attach a TOD to an IRA? [And can this sort of thing be done with a 401(k)]? I thought that all we could really do with an IRA was to name beneficiaries

Naming a beneficiary for an IRA or a 401(k) effectively is placing a TOD (Transfer On Death) on the account.

a spouse can override the named beneficiaries.

Not always. If the owner is already married when they open the 401(k) account, the spouse is the default beneficiary, and must give up their right to be the beneficiary if the owner wants to name another beneficiary. If the owner names another beneficiary without the spouse giving up that right, a court is likely to award the account to the spouse if the spouse sues. However, when the owner of the 401(k) gets married after the 401(k) was opened, and there were already named beneficiaries (like a former spouse), the new spouse may not be able to override the beneficiary designation even if they hadn't given up the right to be the default beneficiary.

Note that the requirement for a spouse to give up their right to be the beneficiary is a Federal law, and only applies to workplace plans governed by ERISA, like 401(k)s. IRAs are not governed by ERISA and are subject to state laws.

AJ
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Probably not, but ignore Tele's reasoning (or lack thereof). The real reason is that a trust would only have 5 years to completely disburse the account, and if the trust is paying the taxes, it will be taxed at the generally higher trust rates. If your kids split get it through a TOD, rather than the trust, they will each have 10 years to fully disburse their account, so they can figure out how to do it best for their own tax impacts.

Thanks for your comment, AJ, and clarifying the timeline to disburse the funds.

Another question regarding estates and trusts. Can they use Schedule K to pass potential tax liabilities to the beneficiaries and have them taxed at a lower rate?
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Just for fun, any chance you'll remarry ?

I know I won't but men are more likely ;)
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Another question regarding estates and trusts. Can they use Schedule K to pass potential tax liabilities to the beneficiaries and have them taxed at a lower rate?

They can, but since the trust only has 5 years to disburse, rather than the 10 years that individual beneficiaries are allowed, it's likely that the overall taxes paid by doing so will still be more.

AJ
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Just for fun, any chance you'll remarry ?

I might need to change my hangout from the VA Medical Center. All the women there seem to be more interested in prodding and poking me or drawing blood.
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I know I won't but men are more likely ;)

There’s a reason why.

This reminds me of a cartoon I saw years ago. Two little girls are playing in a sandbox and one starts talking about how wives shop for food, cook meals, clean the house, wrap gifts, wash clothes, raise the kids, drive everyone around, bake cookies, help with homework, and go to work. The other little girl thinks for a minute and says “When I grow up, I think I’ll get one.”

AW
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I believe that I have been very respectful of OP, have asked may open ended questions, and am well aware that this is a public board that most people do not necessarily want to air all personal details - JAFO

You have been respectful yet still have asked thougt provoking questions. And I appreciate that.


"In fact, it bothers him in TWO ways. First, enabling what he considers irresponsible behavior. And, second, unequal disbursement because he still loves his son despite everything that has happened (or at least, it sounds like that is the case)." - 1pg

Yes it does bother me and in exactly the two ways you put it.


Or perhaps more ways than that. I believe the angst will continue until he understands why it bothers him. - JAFO

I think I understand why and it is the way described so succinctly by 1poorguy. I know you have suggested that perhaps a part of it is envy on my part for him choosing a carefree path through life, one that I deep down wish I had chosen. I don't think this is part of it.

I enjoyed working and always have. When I got into higher level management I enjoyed making significant decisions that had broader impact. I gained a lot of satisfaction from doing an effective job of running my department and for the most part was well liked by the other managers and the people who worked for me. And frankly I enjoyed the attention I got from the various account teams. Some of those people are now some of my best friends even though the business relationship has ended.


"It's just right or wrong for him, and it seems both options are right AND wrong, hence the "angst"." - 1pg

Exactly. And that seems like the very definition of a dilemma.


Which leads back to my questions. If he really understood why he was so "angsty" it would probably be easier for him to resolve with inner peace with his decision, whatever it might be. - JAFO

The thought provoking dialogue in this thread has helped me articulate why I am so "angsty" To summarize, there are three elements that grind against each other. The firtt two are paraphrasing 1pg's observations.

1) I have always had a high work ethic, very goal and achievement oriented and it has led to a good life, a comfortable life with a lot of satisfaction for being successful and for self reliance. It simply bugs me to become an enabler for my ner-do-well son who has shown a certain laziness in his work ethic and who also has acted a little entitled at times. My sense of this about him is magnified by the obvious contrast with his sister.

2) In spite of everything I do love him and don't wish him any ill will. And for that reason, I question if I am being unduly harsh if I do go with an unequal distribution.

3) He and his his sister already have a strained relationship that built up over the years. It is rooted in her being a high achiever and seeing her brother as hustling his way through life, not to mention capping it off with his felony. My concern is that an unequal distribution will lead to even greater friction. I doubt their relationship will ever heal but adding friction is something I have to be concerned about.

Here is one point of information for you all. If the unequal distribution went the other way, ie my son gets a much bigger slice, I am pretty sure my daughter would shrug it off with an "Oh well" and get on with her life. OTOH my son will feel screwed. And even though I am dead, I would rather him not spend the rest of his life hating his father. Plus he very well could make trouble. He has a temper and a vindictive side that he inherited from his mother. Not meaning to bash my ex, but it is true.


I do not believe that I have been doing anything different. My questions were all directed to lead to self-reflection and to make him think why and the potential consequences of his different options. - JAFO

Yes, and thank you.
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It will be interesting to see what he ends up doing (should he choose to share it with us).

1poorguy


------------------

I will do that but any decisions will be a long way off. I am the sort of person who thinks things over before committing but this has drug on way longer than anything else that comes to mind.

But, I need to discuss this with my daughter and need to find the right time and circumstance to do it. I would rather do it face to face but she lives in FL and I am in TX. I refuse to fly so Tampa would be a three or four day drive each way. I don't plan on dying soon, so I assume I have time to make this happen. It would be nice if she would come for a visit but she is very busy.

Someone suggested a book, Ruling from the Grave, and I want to take the time to read that.

My son will reach a crossroads soon when he gets out of prison and I need to see what develops at that time. He could be facing additional charges and may get more prison time or there could be probation.

After all, the a visit to an estate planning attorney to get advice and possibly commit decisions to a will and/or trust.

I will probably be back on the board with this topic a few times as these events unfold for more advice and perspective. I appreciate you all's patience.
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... any decisions will be a long way off...

Sometimes done is better than perfect. I'd suggest a simple will or trust that splits everything 50/50 for now, and then tweak it, or write a new one entirely, as your plans evolve.

Some estate planning attorneys recommend an annual review anyway. Personally, I've found every 5 years is enough. Even when DH's and my circumstances don't change, laws change.
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I would like to thank everyone who has contributed to this thread. It is very important to try to get these things right,and a thoughtful approach is best.
I can speak to this from both sides as one who inherited and as one who will be deciding how to split our assets upon our death.
My father left his estate to four children equally,even though one of those children was much more in need than the others. The decisions the three of us made in reference to the fourth child that needed more help were difficult for us, but with 20 years perspective on the situation,worked out ok.

My dilemma is similar to BHM's situation in many ways,2 children with one currently dealing with life better than the other.
My initial thinking,and our wills are currently written this way, is a 50/50 split without conditions.I believe that we will be gifting our children with funds and observing the result,which may change my thoughts towards 2 trusts instead. I hope we are young enough to figure this out,but all any of us can do is our best.
My largest concern is a windfall inheritance can easily backfire and do damage. Much to think about. Thanks again for opening this thread,there is great value in the back and forth here.
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bighairymike: Thank you for the kind words.

"The thought provoking dialogue in this thread has helped me articulate why I am so "angsty" To summarize, there are three elements that grind against each other. The first two are paraphrasing 1pg's observations.

1) I have always had a high work ethic, very goal and achievement oriented and it has led to a good life, a comfortable life with a lot of satisfaction for being successful and for self reliance. It simply bugs me to become an enabler for my ner-do-well son who has shown a certain laziness in his work ethic and who also has acted a little entitled at times. My sense of this about him is magnified by the obvious contrast with his sister.

2) In spite of everything I do love him and don't wish him any ill will. And for that reason, I question if I am being unduly harsh if I do go with an unequal distribution.

3) He and his his sister already have a strained relationship that built up over the years. It is rooted in her being a high achiever and seeing her brother as hustling his way through life, not to mention capping it off with his felony. My concern is that an unequal distribution will lead to even greater friction. I doubt their relationship will ever heal but adding friction is something I have to be concerned about.

Here is one point of information for you all. If the unequal distribution went the other way, ie my son gets a much bigger slice, I am pretty sure my daughter would shrug it off with an "Oh well" and get on with her life. OTOH my son will feel screwed. And even though I am dead, I would rather him not spend the rest of his life hating his father. Plus he very well could make trouble. He has a temper and a vindictive side that he inherited from his mother. Not meaning to bash my ex, but it is true."


My suggestion - rank your reasons 1, 2 & 3 in priority order for you (and associate some relative weight to each (perhaps out of 100%. Then analyze what sort of distribution each reasons suggest to you. Multiply by your weighted ranking and see which way the scale tips. Decide if you can live with the result.

Also, do not forget that while you are alive have decision making capability, you can always revisit and revise your plan.

Only you can rank them in order and give relative weights.

If I may, your point 1 above seems to favor disproportionate distribution to D, in some manner.

Your point 2 seems to favor equal distribution (ignoring de minimis personal property altogether, for ease, or perhaps make a rough estimate of value of personal property and give him a slightly more cash to counterbalance).

Your point 3 also seems to favor equal distribution (subject to same parenthetical comment).

It is up to you (and your spouse, if any); it has always been up to you.

Regards, JAFO
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JimKredux: " My largest concern is a windfall inheritance can easily backfire and do damage."

The book: "Sudden Money: Managing a Financial Windfall" by Mary Martin and Susan Bradley sheds much light on this topic.

The same concern is why many trusts with independent trustees pay income until age x, then payout 1/3 of the trust corpus (so the beneficiary cannot blow it all immediately or at at once), continue to pay income until age y then payout 1/2 of the remaining trust corpus (approximately another 1/3 of the original amount), then pay income until age z, when the final trust corpus (again, approximately 1/3) is paid out.

That kind of strategy can prevent it from all going to wine, (wo)men, and fast cars and flashy jewelry. And you pick ages x, y, and z. Or leave it all in trust, like inparadise writes about with the beneficiary eventually becoming the sole trustee after a period of time serving as co-trustee with an independent trustee. Lots of options with a trust or trusts.

Regards, JAFO
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That kind of strategy can prevent it from all going to wine, (wo)men, and fast cars and flashy jewelry. And you pick ages x, y, and z. Or leave it all in trust, like inparadise writes about with the beneficiary eventually becoming the sole trustee after a period of time serving as co-trustee with an independent trustee. Lots of options with a trust or trusts.

What we are doing is a bit more complicated than that. We have about half our assets in tax deferred accounts which would go straight to the kids at our death via beneficiary definition, the taxables going into the trust, including the returns from sale of real estate. There will be a decent income from the trust, depending on how they decide to invest it. We may reconsider that as we make more and more Roth conversions, and only have them directly inherit the T IRAs, so they can pull the assets out over 10 years. But anything that goes into the trust is immediately accessible to them when they reach 35. We will only be in our 60's when that happens, so we anticipate those trusts will never have to happen other than to simplify transfer of assets. This is a strategy if both of us die at the same time before they have had time to settle into a career and put into practice the money handling strategies we have taught them over the years. Retirement has us together almost all the time and increased the chance of simultaneous wipe out compared to work days.

Yes, you can make it say just about anything, no doubt subject to some limitations in the law. Please keep it simple. Trust can be a royal PITA for the recipient and not always practical. DH inherited a small trust from his mom, that winds up costing us more in taxes and opportunity, as well as fees for the co-trustee and second tax return, than it would have had he inherited the money directly instead of via a trust. It consists of less than 5% of our assets, yet it takes up more time than the rest of our investments combined. Our kids will inherit this trust if we don't spend it down on DH's care should he require it. I would rather spend that trust down and free up our savings for the kids to inherit without the PITA restrictions. Since MIL's small trust will split once again between our kids at DH's death, it won't be hard to dissolve that trust, except there is no provision to do that in the 3" thick binder detailing the trust. We let it ride so we don't have to spend more on lawyers fees to figure it out. Been there, tried that, everyone left the table confused.

FWIW,

IP
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That kind of strategy can prevent it from all going to wine, (wo)men, and fast cars and flashy jewelry.

If I die tomorrow, I hope all of the money/assets get spent and I suspect it will go to travel, a slightly better car unless that just means my cars, and slightly earlier retirement. Since my youngest became the executor at 21, I am not worried about what happens to all of it after my death. I hope it all provides a ton of enjoyment. No trust except the trust in my kids.
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Sometimes I find it helpful to consider the extreme cases in figuring out where I stand on something. Two extremes are disability vs tough love.

The disability view is that he has a mental health condition that prevents him from fitting in the way you and your daughter do. Before we have kids, we all have ideas of who we want our kids to be, boy or girl, athlete or intellectual, gay or straight. Loving parents know we can't force our kids into our fantasy box and love them for who they are. This view says recognize he can't change, accept him for who he is, and support him.

The tough love view is that he is fully capable of supporting himself but chooses not to. Bequesting significant assets merely enables him to continue to make harmful choices. Some people need to hit bottom before getting their lives in order. If this means being homeless and hungry, so be it. If it leads to early death, it's on him.

If you go the tough love route, how will your daughter respond? Is she on board with tough love? If not, would she would feel compelled to support him to prevent the worst? In that case, tough love shifts your responsibility to her. Providing your son with the resources needed for him not to be a burden to your daughter is a gift to her, not to him.

I have seen this play out with my siblings and cousins and lean towards the disability side. I have not seen any of them change. They are who they are. The route that seems to work is to find a way provide ongoing basic support. Anything more quickly gets lit on fire and they are back to the beginning. If I were in your shoes, I would look into trusts and other mechanisms to provide him with ongoing basic income.
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