I read an article like 5 to 10 years ago, I think it was in Wired for some reason. Dude just said fuck it and walked away from it all and made a little shanty shack in the middle of the woods. He survived by breaking into nearby homes/cabins and stealing food. I guess he forgot to steal a toothbrush and toothpaste, because at some point his health, in particular teeth, got so bad he let himself get caught. If there was anything impressive about the story, it was his ability to stay hidden in the woods in spite of several attempts to track him down.
I think a lot of homeless people just do not want to deal with the BS required to own a home, have a job, and all the responsibility. One thing I took away from playing Red Dead Redemption 2 was, there was a time when you could live off the land, do some hunting and trade furs for basic supplies and could live on your own schedule and be your own boss. Really hard to do that these days. Essentially being homeless is the closest thing.