Greetings, Goodfernuthin, and welcome to Fooldom.<<I need to plan tax stratagies. If I roll over some of my IRA funds to a Roth next year (in addition to the $2,000 new IRA contribution for that year), would it be a smart move to spread the taxes due over four years, since we will probably be in a lower tax bracket when my spouse retires? >>Actually, it's a moot point because you will have no choice in the matter. If you roll a traditional IRA to a Roth in 1998, you MUST spread the income and taxes over a four-year period.<<Also, we (I) need to plan what to do with the 401K plan funds. In addition to increased choices of funds in the plan, we also have the option of leaving the money in the funds when my spouse retires. We, having received the projection of pension amount and social security benefits, find that we will need to take some distributions from the 401K and/or IRA's as income. I have a financial planner (he does not charge a fee, just gets a commision on funds he sells, and yes he is a certified, passed the test, with a masters degree, financial planner). He suggests that we move the money from the 401 K funds into a managed fund, managed by a fund manager which can be changed at any time if we don't think the performance is acceptable. What do you advise here, Pixie? Or can you recommend reference material, books etc. to help me? >>No advice, just a comment. I prefer the flexibility afforded by the IRA. If I'm dissatisfied with returns or management of the money, I can switch at will. I can't do that easily within a 401k. Your CFP is right on with that point. Whether the investments he has recommended fit your risk tolerance and desires is for you to say.<<To add a third question: What do you think of my becoming an independent contractor (part time sales) and itemizing business expenses separate from our personal retirement income? Would this help our tax situation? I know nothing about reporting business expenses yet. Sorry the message is so long, but you probably need a complete picture to answer the questions.>>Help your tax situation in what regard? If the business is successful, you'll make money and have more income to declare. If it loses money, you'll garner some deductions. Which do you prefer? Your CFP knows your circumstances, so he should be able to offer some guidance to you in this regard. It's just not a question we can answer here with any degree of accuracy.Investing in retirement poses some challenges to you. You want your stash to last, but you also want to take income. In that regard, you might want to read messages 228 through 250 and 292 through 295 in this folder. They cover many of the issues you are now facing, and may help you in some of your decisions.Regards….Pixy
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