I volunteered at a shelter and soup kitchen before. I'm not a psychologist but the way a lot of the homeless act, a lot are bipolar that self medicate. The veterans have PTSD.
I met a plumber before who got all his tools stolen when he was asleep in the park. A bike messenger company the shelter keeps in contact with gave him a job.
Rent prices fucking suck in the city though so I don't even know how they would get a place to live with 2 months rent upfront. Can't even get a bank account without an address so credit check is out of the question. They probably been thrown in jail a few times so background check is all fucked up...
I get it how people can just think they are lazy, but starting from the bottom is hard.