My wife is a social worker for the VA. Her job is housing homeless vets. From what I hear, clients typically struggle with mental illness, PTSD, military sexual trauma, and more. Some have what they need to get back on their feet and some are probably never going to because of mental illness. Yes some, and it sounds like a minority, have learned to manipulate the system as part of their survival strategy.

There are also some who just want to be left alone. Around here they live in the National Forests up in the Cascade Mountains. The problem for them is age. Right now the reclusive Vietnam Vets are coming out of the woods. They are just too old to survive out there on their own out there.

On the whole safe housing is showing to be very important first step. Homeless life does include a community on the street. It is typically a community that is not going to be supportive of positive change. Each member is experiencing their own untreated issues.

Removing the negative social elements and temptations first appears to be one of the important benefits. If you're an addict having friends offering you a hit is not very helpful.

Thus, for my wife, building relationships with housing agencies and businesses is a big deal. The landlords/managers with endless patience, understanding, and strong boundaries seem to do best.