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Can mutliple Roth accounts be held under one custodian or would those have to be established through separate custodians?

You can do it all with one custodian. They key is that in a recharacterization only the specific account's performance is part of the equation.

The unquoted part of your response tells me you've got the gist of it enough to analyze your particulars, but feel free to come back for more help or a sanity check. You commented that custodians must hate this, which raises the point to make sure you check about fees, both transaction and maintenance. My custodian charges no maintenance fees or fees for conversions or recharacterizations, but these can eat up a lot of gain in a hurry with some custodians. Checking up on that beforehand is part of your due diligence.

Rule Your Retirement Home Fool
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