This always comes to mind when I see folks on the street here in NYC/Brooklyn. Is it too simple a solution? Is a dense metro better in some ways?
So they probably still have family connections there, friends, maybe a church or AA group, case worker, friendly coffee shop owner, etc. They aren't any more eager to break these ties than you would be.
cold isnt a big problem if u know what ur doing. during the summers u can spend all day at the beach and that makes up for it.
spend the day at the library working on the computer. police and security are relatively lax so long as you know how to blend in, some homeless people are less socially adept and dont take care of themselves so they are magnets for reprisals in a manner of speaking.
I actually think it's a bit infantilizing to suggest that any otherwise capable person would choose sleeping on the streets or in shelters over a basement apartment in a cheap, boring town.
Speaking personally, I'd prefer living in quite literally any town in the entire country if it meant a roof over my head.
Almost no one "prefers homelessness" to anything else per se, but they may decline the terms on which housing is offered. For example "break all your social ties and move away from the only city you know" is extremely hard for anyone to accept.
Look at some other conversations in this comment section! A lot of people want to "solve homelessness" but a lot of them also don't care what happens to the homeless people on the way. "Come with us, to a place you've never heard of and know nothing about, where all your needs are met"? No thanks my man I have read Maus.
FWIW I think it's really admirable of you to maintain those community connections, not everyone would do the same.