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Thanks Baraka I'm going to check out your suggestion, I expect something as old as 1825 should be online somewhere.
And thanks Jetée for that interesting article. I hope that kid doesn't end up getting shot. I was meaning books when I first wrote the post but any documentary films would also be of interest - especially historical ones. There must be a few depression-era ones. I think what I meant by 'literary' was that the account, book or work would be generally considered a work of literature, have been published by a known publisher and be somewhat well-known.
Even if the author wasn't actually homeless the whole time but was pretty close to that lifestyle - e.g. Charles Bukowski. And even if the account wasn't autobiographical but was related by someone else who was close to them but not actually living that life - e.g. Clarence Rook's Hooligan Nights. This can include books about hobo types who may have been illiterate but were interesting enough characters or had interesting enough lives that books were written about them.
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