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.
Take a quick peek at Maslow's hierarchy of needs please and map both their situation and what you're asking of them.