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If you're willing to just come and be a homeless person for a while in any decently populated area, you'll most likely be able to get a free hotel room. You just need to call Vermont Economic Services or 211 and explain you've been sleeping outside and you heard there were rooms available...

Psychonauts 2 is coming out this year.

There's a pack of crusties in Life is Strange 2. You end up going to Humboldt and trimming weed with them. Seriously. There's also a game called Where the Water Tastes Like Wine that has a strong old-timey hobo vibe.