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" What if I roll my 403B nest egg directly over to a Roth IRA? Then I'll never pay any tax when I begin withdrawing (after 5 years & at age 59.5)?"

Uncle Sam has forseen this one and won't let you do it.
You can get your 403B into a Roth by this procedure: You roll the 403B into a TRADITIONAL IRA. No taxes due here.
You can then roll the traditional IRA into a Roth, paying the taxes (not penalty) on the amount so rolled. You are allowed to do this if your AGI qualifies you for such a rollover.
The problem is that while the rollover does not disqualify you from having a Roth (assuming you were entitled to a Roth in the first place)
your AGI on which you will pay 2001 tax will include both your usual salary and investment income, but also the amount of the rollover on top of that, at which you will pay tax at your marginal rate or maybe above what would otherwise have been your marginal rate.
You run the numbers, but you may do better to leave the traditional IRA alone and pay the tax at what the bracket will be when you are 59 1/2. On the other hand, if you are going to invest aggressively in stocks and you believe the market will be a lot higher in 5 years (I do) you may prefer to swallow the tax bite and make the conversion.
But eventually, Uncle WILL get his!
Best wishes, Chris

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