I'm a novice at any of this. I'm 55, just retired, have about 1M in 401k and about 1M in taxable/brokerage and my expenses have always been very low compared to those figures - time to spend! I've been staring at this Roth conversion stuff for quite a while and feel like it's a hole that gets deeper and deeper. What about how that affects SSI taxes? What about how it affects medicare or ACA or all these other things?
Last year, my state got rid of taxes on "retirement" income for those 55 or older and that includes Roth conversions - so those just got 5-6% cheaper.
Thinking about all this, I chose to take retiree medical for $10k/year for now as that's a one-way door. If I drop it, then I'm on ACA, whatever that looks like for the next 10 years. I can change my mind in a few years if I'm pretty sure the ACA won't go away or turn really ugly.
I ran across an advisor's video talking about how most people make a mistake when doing yearly conversions by doing the conversion at the end of the year and projected many years down the road, that's worse than doing it at the beginning of the year or doing 2 conversions during the year, etc. because the sooner money goes into a Roth and starts earning tax-free, the better.
So I've done a few simulations and I'm more puzzled. Now I'm around to using "Retiree Portfolio Model v24.0.xlsm" from the Boglehead forum:
https://www.bogleheads.org/forum/viewtopic.php?t=97352
This seems to be the most comprehensive model I've come across.
Inputting round numbers for expenses, etc. and then just changing the Roth conversions, I get the following outputs at 94 years old (when someone will need to be paid to care for me if I'm still around).
No Roth conversions: Ending at 5.36M, total Federal Taxes of 1.29M
13 years 55-67 of 60K: Ending at 6.44M, Federal Taxes of .678M
4 years 55-58 of 200K: Ending 6.85M, Federal Taxes of .523M
So according to whatever crazy stuff I've done with this spreadsheet, it says that it's best to go up to the end of the 24% bracket and convert the majority of my 401k over ASAP, compared to a longer set of conversions staying in the 12% range.
I'm a bit biased here as I like the idea of paying a chunk of taxes now and locking in the future a bit. I don't think they'd ever change the rules on existing Roths, but to change existing tax rates would be easy and I feel a bit of doom and gloom ahead with fiscal easing and the deficit. If future taxes end up lower - boo hoo/don't care - but if I plan for a large tax bill and it doubles or something, that would hurt.
I'm not sure I understand these results and suspect that I'm doing something wrong.