Craig Wear, CFP® advises do-it-yourself taxpayers to consider hiring an experienced professional (preferably a CFP) for at least the first couple years of performing Roth conversions. He recommends this to ensure proper cadence, avoid mistakes related to tax-bracket or Medicare thresholds, and to maximize value from conversions.
I highly recommend that if you're a do it yourselfer on your taxes, I think it's worth it to you to hire a professional, at least for the first couple years that you're doing Roth conversions, until you really get the cadence down of what you should be doing. If you are a do it yourselfer and you've got your own spreadsheets about how much you should do, or you have some paradigms about being afraid of getting up to the next tax bracket or Medicare issues and those kinds of things, then I would suggest that you get with somebody that's really experienced in dealing with Roth conversions. And of course, that's where our CFPs around the country come in is to help you to really understand that you're getting the best bang for your buck and that you're really doing this the right way.
