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As previously recommended, this is a year that professional help would be a very good idea.

With your daughter medical situation consulting someone who is familiar with legal issues associated with Medicaid and a disabled child would also be a good idea. With my mother-in-laws passing we are dealing with a relative that is an Disabled Adult Child (Social Securities term). There is a lot to learn.

Currently, I have about $60,000 in my Traditional IRA. Does the amount I have contributed to the traditional IRA vs investment gains matter when determining tax implications for a rollover? Or do taxes simply relate to the total in the account at the time of the rollover? Would that rollover amount contribute to our overall income for the year? I am expecting we will be around the $75 - 80K mark for 2020 income between my wife and I. If I do the rollover I would just need to be careful to not push us up into the next bracket, correct? Is 80K the current cutoff for married filing jointly? What is the time frame for doing a conversion in 2020? Is it 12/31/20 or 4/15/21?

Where any of your contributions to the IRA taxable? If not then the amount you contributed doesn't matter for the rollover.

It is no longer possible to undue a ROTH conversion. Once converted it is committed.

Conversions are taxable in the calendar year converted. Limit is 12/31.

Partial ROTH conversions are allowed and multiple can be done in a calendar year providing IRA administrator allows it. The taxable part of a conversion is taxed as regular income.

$80,000 reference is likely regarding federal taxes. You should also check state income tax.
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