this seems very difficult if you aren't a member of a protected class. can a young white healthy male freeload easily?
I don't know about race, but I did read a piece by a young man who viewed homelessness as a sort of urban camping. He didn't use drugs and he didn't beg-- he found enough odd jobs.
From Mike Darwn's Chronopause, an essay titled "Would You Like Another Plate of This?", discussing people's attitudes to life:
Conclusion, graphs, and references in article. As usual, I recommend reading Chronopause.com as Darwin has many good articles; to quickly link a few: