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I have yet to travel, so take this with a grain of salt (anyone with real experience, please feel free to expand on or correct me). I'd say look into laws that will affect your lifestyle in different states. Plan to hitchhike? Probably don't come to Florida bc it's illegal here. I would highly highly highly advise against being houseless in Broward County especially, cops there will take any opportunity to beat and degrade you. It's also illegal to feed the homeless there or for homeless people to have possessions on public property for a certain amount of time.
Hit up people in/that have traveled to the specific areas you wanna know about.
I can't speak for other southern states but in FL I've seen almost exclusively religious organizations that have services for houseless people.
Ya, i still don't know why people think that Florida is a good place to go to, there is SO much evidence to the contrary....
I hope that alligators and pythons reclaim that entire state for their own.