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Does that mean we need some kind of big brother/sister program but for the homeless? Would having one capable volunteer who met with them for an hour a week or something and could advocate and help them navigate the system make a big change?

I really struggle with this because it feels like helping as much as possible is the only moral stance to have, but I also question what level of responsibility the homeless have for their own situation. If we keep approaching them with these 0 consequence strategies does that encourage failure? Would the second guy who was smoking meth have benefited if he got thrown in jail for two months, forcing him into sobriety and then released into some kind of temporary housing with strict work and curfew rules?

We balk at the idea of limiting someones freedoms, but it seems like a mercy to take someone who is killing themselves and endangering others and putting them through some kind of rehabilitation that forces them to get physically and mentally healthy. It might be a relief to have a schedule and safety and some kind of guiding hand.

>>ericmc+(OP)
The fully honest answer is that I don't know. I have some first-hand data but no actual expertise in this area. But my personal advice is this: one of the best things you can do for a homeless person is simply to talk to them, to make them feel seen. One of the worst things about being homeless is that you become invisible. For many people that's almost as bad as the physical hardship.