Craig Wear, CFP® advises that most people—regardless of income level—can be good candidates for accelerated Roth conversions but must ensure the tax on conversions gets paid. He recommends making estimated tax payments promptly (cutting a check or using electronic transfers) when a conversion occurs mid-quarter, and alternatively adjusting withholding if withdrawing from other deferred accounts/IRAs to cover the tax liability.
Whether your income is low or high, you're probably a great candidate to do accelerated Roth conversions. And so you want to really make sure that you get the taxes paid. And the easiest thing to do is just if you do a conversion and let's say it happens to be during the middle of a quarter, then just make sure that when that next estimated tax, tax payment date happens, that you cut a check. Or we, we just use the electronic transfers now to make all that stuff work. If you happen to be withdrawing money from deferred accounts, other IRAs, then just maybe adjust your withholding.
