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Greetings, TheOthermfa, and welcome.

<< For example, if I'm sitting on a $1M IRA (dream on...), can I in fact transfer $100K of it to a Roth, and will this result in an additional $25K in taxable income for 98,99,00,01?>>

That's correct in all aspects. You may roll part or all of existing IRAs to a Roth IRA starting in 1998. One-fourth of the amount rolled is declared as income in 1998 and each of the following three years.

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