No. of Recommendations: 2
Any rules of thumb on doing this, or any methodology that would avoid reinventing the wheel?

Well, a large part of it depends on what your marginal and average tax rates are now, compared to what you think they will be in retirement. If you think your rates are higher now than they will be in retirement (i.e., you'll have less taxable income in retirement), then I would lean toward getting the tax break now. If you think your rates will be the same or greater (i.e. you'll have as much or more taxable income in retirement and/or you think rates will rise), then you would probably want to pay taxes now vs. deferring them.

Also, Stupid Question #47B: does one pay capital gains taxes on investments in an R-IRA?

No. There are rules that you have to follow (found in IRS Pub 590) but assuming that you follow the rules, all withdrawals from a Roth IRA are tax free.

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