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.

that's a variable you can ignore if you want to.

...... if *i* had a tonne of money in XYZ, i'd want to dump some just to diversify ....
if i dumped it all for 'tax' reasons, i'd definitely want to diversify the re-investment.

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

the chart says they will.... so that's a reasonable assumption

.... and shows maybe why my gut says it doesn't work -- those are top marginal rates .. if you dump everything, average rate will be near top marginal rate, if you dump only what you want to spend, average rate could be much lower.

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.

another thing ,maybe, .... i think to be totally legal, you have to be out of Calif an entire tax year to avoid their tax ... so you have to hurry

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