I doubt we will get to the end cause of all the issues in a conversation here, but my understanding is that getting people whatever kind of help they need is vastly easier if they have a roof over their head and a permanent address.

I agree. But one of these 2 people had subsidized housing through the state. It was incredibly cheap rent for the area. Cheaper than any housing can be just from building more. But they still lost the place after a few months because they did not pay rent and instead bought toys and quit their job. They were receiving money from the family, work opportunities from the family, the family walked them through all of their legal and bureaucratic needs, and the family took care of their children. But it was not enough.

For this subset of people, I don't see how you can help them without managing their finances for them. Even if you completely manage their finances, how do you help them if they just quit every job they get?

I never really thought about it much before them, but I think pretty often about the problem. How do you help someone who can't be helped? Even if you gave them free housing and a weekly allowance, they would still find a way to not have money for food before the next week.