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Being homeless in the right city (ex. San Francisco) is awesome. You don't have to work, you can get food stamps food, your time is all your own, etc.. If you want a slightly more stable life, you can earn a minimal amt of money and rent a storage locker, join the YMCA for showers, etc..
Being homeless in the wrong city (ex. Chicago) sucks, due to terrible weather, much less resources, and hard times hustling, due to widespread poverty.
I encourage everyone on /out/ (who has not thrown their life away to children) to spend some time hitching or train hopping, exploring your region without the responsibilities of a steady job, renting, etc..