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My friend has about $500K that he needs to last for the next 11 years...He wants to be able to count on an inflation-adjusted $50K withdrawal every year for the next 11 years from that $500K...
Does anyone have advice for safer investment vehicles that are pretty well guaranteed to protect the principal, with maybe some small return?

There might be an annuity-type product that would give a 10% payout for 11 years. Because the issuing company is almost certain to make out better than your friend by taking that risk, one might issue such a financial product. It might be required to start withdrawals in one year rather than immediately, and pay high fees, plus there's a 100% chance the money will be gone regardless of what stock/bond/whatever markets do. But if your friend wants to pay through the nose to remove all market risk, have a look. (Of course, there's risk in the solvency of the issuing company, right?)

I know that there are annuities for various terms, and maybe the 11-year ones aren't at 10% or don't have inflation increases, but you can look for something. If the numbers aren't what your friend needs, at least you haven't left that stone unturned.

Maybe one way to back-stop a tiny amount of risk is to accept that he *might* have to do a reverse mortgage if the small amount of risk bites at just the wrong time. The problem is, he's asking for a greater percent payout that an accepted "riskless" investment (T-bills) can provide.
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