Earlier quoted context omitted.
Whenever I see someone who is quite clearly very recently homeless I give them as much money as I can afford to, like $50-100, because I feel like it can get them out of homelessness. When I see someone completely out of their mind I don’t feel like anything I can do will make a material difference, just get them different levels of stoned for the next 3 hours.
When you give $50-100, please employ them to do a task. Ie. "Here's $50. Go and buy me some ice cream. You can have another $50 when you bring it to me". It discourages begging and encourages an entrepreneur mentality.
Why does your goal have to include putting them in some weird spot where youre holding power over them to teach some "entrepreneur mentality". Most of the temporarily homeless population is embarrassed to ask for money, just treat them like an adult if youre going to offer help.