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I'm interested in rolling over my 403b to a Roth IRA, and not getting killed on taxes when I do it. We are a married couple: my wife makes more than $325,000 a year, and I make $0. I am wondering if we can use this fact to our advantage. I posted this question elsewhere, and was instructed to post here. Can anyone help? I'll summarize the key points below, but you can see the previous post and some good discussion here:

The corollary to this question is whether it would be smarter to simply roll over to a Traditional IRA and pay taxes when I withdraw, vs. now.

Key facts:

* As of a few years ago, 403b plans can be rolled over into Roth IRAs if you pay the tax liability owed. (!) As of a few years ago high income earners are not restricted from rolling over/converting in this way. (!!)

* I have $250,000 in a 403b plan currently administered by Fidelity. I potentially want to roll over/convert this entire amount to a Roth IRA, if that is in our best interests.

* My wife earns more than $325,000 a year. This income is stable and it will increase substantially in coming years.

* I earn $0 and have no interest in returning to work anytime soon. I have not worked or sought work in 3 years.

* We will both reach retirement age in about 25 years.

* My wife is on track for a very good retirement: her workplace has a traditional pension that offers from 50% to 60% of her highest three years of earning. Her workplace also has her enrolled in a traditional IRA that she is maxing out every year. The pension alone should yield her $200,000-$300,000 a year by the time she retires.

* I like investing and am generally successful with it, so I probably would be served by having my $250,000 in a Roth IRA in a brokerage account.

* We will not need premature access to any of my Roth monies now or later. We own various insurance that will defend us against most unforseen disasters.

* We pay income tax to the federal government and the state of California.

* A key advantage of the Roth for high earners (as I understand it) is that withdrawals don't contribute to income in the sense of pushing you into higher marginal rates. Given my wife's probable pension, this seems significant.

I am wondering if some scheme like "Married filing separately" for one year might allow a legal way for me to roll over my 403b to a Roth IRA without getting killed on state and federal taxes. After all, my income is $0.

(and in an unrelated question, I am wondering if the amount of tax we are now paying is unusually high. For last year, I believe we paid 34%+ of our income in income taxes alone.)

Thanks in advance for any help you can offer. Happy to repay the helpful with a bumper crop of heirloom tomato seedlings now, or bushels of tomatoes later. That's my work these days.
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