I'm from a small town in Oregon that sees a lot of nomadic traveling folk, either homeless or lifestyle (the PCT comes through the area, for instance), and the town is generally pretty receptive of these people. Growing up I would hang out and spend time with them, just chatting and playing music and enjoying the area. I carried that to adulthood and I now live in Portland, where the homeless problem is quite severe.…
https://www.theguardian.com/us-news/ng-interactive/2017/dec/...
If you send someone half way across the country, it will be difficult to return. They also mention Key West contractually bans anyone who returns from using their homeless services.