No. of Recommendations: 2
Or, y'know, just do a mid-December IRA withdrawal for the approximate amount of what your tax will be, or the safe-harbor amount, and have 100% withheld.

I prefer "parking" the RMD in my taxable investment account at the beginning of the year and temporarily invest it in an investment that generates non-taxable income while I decide whether to spend a portion of it and decide which securities I should invest in.

Now I'm starting to think that maybe I'll stop the withholding from our monthly pension and let that IRA withdrawal be our entire withholding. The first few years after I retired I tried to juggle the withholdings to be close to the taxes owed, but it was always wildly off and a real PITA. Either it would be way too low and I'd have to write a big check, or way too low and I'd get a big refund.

I mucked about with having taxes withheld from Social Security, pensions, and RMD initially and discovered it to be a highly unpredictable way for paying taxes: you either had too much or too little taken our for the IRS, for the California FTB, or both. I too hated writing big checks to submit with my tax returns.

I switched to making estimated payments to the IRS and California FTB. So far no underpayment of taxes to either and only a few hundred dollars of overpayment that I apply to the first quarters estimated tax payments. So between 01 and 15 April; I complete last year's tax returns, schedule my quarterly payments to the IRS and California FTB and forget about taxes until next year.
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