Something else to think about is that the IRS is probably all over these cases, too. Someone who gets $400,000 — or even just $10,0000 — in “donations” from total strangers would seem to have a tax liability here.
Yes, maybe. With some legal help the funds and their use can be structured so that no so much of the funds go directly to the homeless person and most go to charitable trusts that directly pay for supportive things for them. A charitble trust can even buy a home, own it, and charge a nominal rental fee to a formerly homeless person, without the homeless person being taxed on the difference between that nominal fee and market rents.