It probably doesn't feel very good, since not a lot of people are homeless by choice. Try fostering an addiction or untreated mental illness for a few years and maybe you'll be close.
If you'd really like to know, you could just go out and talk to one for a bit. They're usually quite happy to chat about things, and you don't need to be afraid of them at all. No Queens alleyways though, that wouldn't be smart.
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