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So I have been creating spreadsheets to crunch the numbers and using online calculators to verify, and I can’t find a reasonable scenario where I wouldn’t be ahead to convert my large (to me) deductible Traditional IRA to Roth. I am in the fortunate situation where I could pay the tax bill for the conversion from proceeds from a taxable stock account. Even considering that it bumps me to the 32% tax bracket in 2018 it still seems to be the best decision for maximizing my future after tax income along with the added benefit that it gives me more flexibility. Am I missing something?

Since the current year tax consequences are a 6 figure impact, I am stressing about this decision. I have met with numerous financial planners over my 20 year investing career and am always disappointed in their lack of insight. Seems like I usually pay for someone’s advise that is less knowledgeable than me. So I’m asking this board if anyone has experience with this. In what scenario would it be a bad idea to convert from a deductible traditional IRA to a Roth IRA when you can pay the current tax bill with outside funds?

Thanks for your help!
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