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.