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Originally Posted by M2inOR
I'm going to be 70 this year, and started my Roth conversion planning 3 years ago when I moved to The Villages. Tip to start it from my Fidelity advisor.
After reading many articles, and doing some calculations, I got a 2nd opinion from Craig Wear. His business is to provide you with a multi-year conversion plan for a fixed fee after looking at your entire situation.
A Roth conversion does not make sense for everyone.
Yes, you will pay more in taxes during the conversion. Yes, the yearly process may subject you to IRMAA, raising your Medicare premiums. Yes it will cost you $$$ in the short term.
For me, it made sense in the long term. Wife and I have both significant IRA accounts AND taxable investment accounts. We paid taxes from our taxable accounts so full amount of IRA converted to Roth were maintained.
We've not taken Social Security yet. I just applied for benefits to start this year; wife will do it next year. Meanwhile, got 8% increase per year plus cost of living increases since deferring taking benefits.
The trigger for us was when we learned RMDs would be significant for us.
Finally, we have enough to live on well into our 90s. Our children and grand children will benefit from this conversion as they will get this money tax-free when we are gone from this earth.
Advice: read the regulations, and hire a conversion expert to make a plan for you.
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I have a "mental block" trying to avoid IRMMA surcharges which I need to resolve. Maybe I will need a Psychoanalyst for that instead of a CFA or CPA.

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I added Craig Wear's Podcast to my list.