Re: How much money do you need?
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About $10 million.
I want enough that after inflation, interest, and taxes (including taxes on the interest!) that I can get $100K/year (adjusted up each year for inflation) with enough principle to last 60+ years. If you imagine that you get a nominal rate of return of 6% per year, that you lose 1/4 of that return to taxes, and that inflation averages 3% per year then $10 million and that you want to be able to spend $100K [2005 dollars] / year then the money runs out after 62 years.
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This is the only reasonable approach to look at the problem. 6% nominal return is pretty reasonable, say munis or the like, and 3% inflation is reasonable as well. 25% for taxes seems is much too low, though - keep in mind that you're talking $600k in income the first year, and it goes up (in nominal terms) thereafter. Also, 60+ years is pretty much the same as forever - you're living off the interest.
My rule of thumb is that you can expect to make ~1.5%/year in real, after-tax returns that are sustainable indefinitely. It surprised me at first that the number was so low, but that's the way it worked out. So, for me, ~$8-10M and a paid-off house.
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