No. of Recommendations: 0
i do think you could easily build a spreadsheet that *might* be convincing .. it would depend on current tax rates, where you think tax rates might go, how you might expect your 'stock' to grow if you don't sell, where you'd invest the proceeds, how much you'd spend from the pile of money ... etc(?)

Where the stock might go is not a factor--nothing at all would stop us from buying it back immediately. "Wash sale" only applies to losses, not gains. The government doesn't mind if we choose to pay taxes early.

I think capital gains rates are likely to go back up.
Historical rates here:

P.S. At one point, we were eligible for a tax shelter pitched by one of the accounting firms that later got busted for it. Basic idea was: pay half the tax to the CPAs and lawyers to get tax owed to zero. That was fun.
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