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How do I report the $400 in earnings? Do I report it as a capital gain (ie treat like I received 1099-div or a 1099-b)Or do I report it as a income and enter it as a 1099-R

Phil got that one for you. Again using your example numbers, you would report a total withdrawal of $2400, with $400 of it taxable.

Also am aware of the option to recharacterize to trad IRA but what I have is a rollover IRA and keeping track of it will be a bit much I think.

You would have to keep track of the non-deductible contribution to a traditional IRA. You could simplify the investment tracking by transferring the recharachterized money to your current traditional IRA custodian. There would be no reason to keep it separate, unless you need to do so for investment reasons.

--Peter
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