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But now I'm curious....

If you're paying a 40%+ tax on a stock sale (as folks in the top bracket are), it might be cheaper to fund current income with a low cost loan. The stock is likely to continue to appreciate over longer holding periods. And 10 or 15 years of a 2% loan should be less than taking a 40% haircut in Year 1. And if you can extend this out to the year of your death, your heirs get the stock with the "stepped-up cost basis" applied, so there's no tax due. You (they) just have to pay off the outstanding loan.

Of course, this only works if you have excellent credit, and can get a long-term loan with a low interest rate.

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