Excellent points.
"Also, do you expect your tax bracket to stay the same over time?"
Unless someone makes SS benefits completely tax free, I will probably be in the middle bracket (whatever the future equivalent of 22% is). One idea that keeps playing in my mind is that 403b withdrawals will also make my SS benefit taxable (so the net effect is more than the bracket percentage) but Roth withdrawals would not.
"Overall, though, my gut feeling is generally to convert each year only what you can afford to pay taxes on without using the retirement funds to do so."
That's fair. If I don't reduce my current retirement contributions, I can probably only convert $10,000 per year. If I leave my current retirement alone but reduce future contributions, I could convert more.
"However, it should be easy to find investments for a Roth IRA that have the same or lower expenses than the investments in the 403(b)."
I don't know about that. All my accounts are currently with TIAA, including my Roth. The universities I have worked for seem very aggressive about negotiating lower rates. The life cycle fund I am in has a 0.6% expense ratio for the institutional funds and a 0.85% expense ratio for the individual investor fund. Some funds at my old employer are below 0.1%.
What about the idea of reducing my current retirement contributions to fund the taxes without withdrawing from the present balance, and doing it in smaller increments?
