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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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