Thanks for posting this against the social incentives right now.
My initial reaction to the situation was similar to yours—wanting to trust SBF and believe that it was an honest mistake.
But there are two reasons I disagree with that position.
First, we may never know for sure whether it was an honest mistake or intentional fraud. EA should mostly not support people who cannot prove that they have not committed fraud. Many who commit fraud can claim they were making honest mistakes.
Second, when you are a custodian of that much wealth and bear that much responsibility, it’s not ok to have insufficient safeguards against mistakes. It’s immoral to fail in your duty of care when the stakes are this high.
Just a few ideas, but note I don’t have enough knowledge to identify all options, or the best option.
Obviously the goal is to maximise the amount Givewell is able to deploy, out of the amount your parents don’t need for themselves. Fees reduce this, but so do taxes.
It sounds like a DAF is not subject to tax at all. If your parents hold shares themselves, they will presumably still be subject to tax on dividends, and on any realised capital gains from trading. I feel like this could be above $5k/year, but it’s worth checking.
It sounds like your idea is for them to invest directly in stocks, rather than using an index fund. (Hence your idea of the in specie transfer of stocks to GiveWell.) This approach is likely to lower fees, but produce a less diversified portfolio with more risk, compared to an index fund. To compare apples with apples, subtract from the DAF fee the equivalent non-DAF index fund fee. By the way, that post you linked mentions an approximate fee of 0.05%, which would be $500 on $1m, not $5k? I am probably missing some detail or other.
If they are set on investing in individual shares and avoiding fund management fees, could they still avoid taxes by creating their own personal DAF vehicle, like a self managed super fund (SMSF) in Australia?
If they are agnostic about when to give, then why use a DAF at all? They can’t take money out of the DAF, so anything they put in there will eventually go to GiveWell. They could instead just donate those amounts to GiveWell. I suppose you mean they want their total donation amount to be as high as possible, regardless of when the amounts are given, so they are not indifferent in a discounted value sense.