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The problem is, he's asking for a greater percent payout that an accepted "riskless" investment (T-bills) can provide.

Even T-bills have risk, unless he were to set up a T-bill ladder that matures with the exact amount that he will need in each of the next 11 years. (And that would mean guessing at his inflation adjustments for each year, too.) If he has to sell a T-bill early and rates have risen, he will lose principal, as buyers will only pay the amount that will get them the prevailing T-bill rate. Since rates are currently very low compared to overall historical rates, there's only a little potential upside, which would occur if rates were to go up.

CDs at an FDIC insured institution don't have a lot of risk, unless one thinks that the FDIC will run out of money insurance money. If that happened, the crisis that would be occurring would probably have resulted in a lot more losses in almost any other investment. Of course, in this case, with $500k to invest, he would have to spread the money across multiple institutions, so as to not exceed the FDIC limits.

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