And so they move to a tent encampment? This makes no sense.
The problem isn't even the bad and catastrophic decisions that homeless people made to get them into the situation -- would that it were -- for the permanent homeless, it is the bad and catastrophic decisions they make on a daily basis to keep themselves in it.
How to treat this? Involuntary mental health incarceration. Police ticketing and other harsh actions to break up the cycle and keep people from being comfortable with their homeless situation. Destroy the social anti-patterns that are keeping people trapped.
Do you know anyway with a child in this situation? Ask them how their offers of money and help went, and what happened when that help was delivered. You may have an interesting conversation.