The right thing to do would have been to spend some of that $400k for a lawyer, to set up a trust with Bobbitt as the beneficiary and the lawyer as the trustee,

The right thing to do would have been to spend some of that $400k for a lawyer, to set up a trust with Bobbitt as the beneficiary and the lawyer as the trustee, put the principal into a no-fee index fund, and distribute $1000 per month, $200 (0.6% of principal annually) to the law firm for trust administration, and the rest to pay for Bobbitt's housing, utilities, food, and fuel, in that order. $12000 a year ain't much, but even if it doesn't keep the wolf from the door, it ensures the door continues to exist. Then you step away from the funding campaign and pat yourself on the back for a job well done. If you're still self-interested, you hold out a secret hope that someone else sets up a campaign for you to reward your virtue and pay it forward. And that's the same thing to do if you win the lottery. Pay a lawyer to handle the taxes and set up a trust, give yourself a (nearly) guaranteed inflation-adjusted income for life, and protect the principal from you and your temptations. Salesmen, scammers, and crooks can only milk you for a month at a time, instead of for everything you have all at once.