For those that haven't been around long enough to remember this being posted here is an article by a guy who experimented with being homeless for a few days...
A similar "homeless experiment" is documented in Adam Shepard's book "Scratch Beginnings: Me, $25, and the Search for the American Dream." After graduating from college, he moved to Charleston, South Carolina with just $25 and a sleeping bag. He had the systemic advantages of being an educated, white male, but he created a back story about leaving a broken home and did not use any particular skills or contacts from his education.
He started in a homeless shelter and worked as a day laborer. After 10 months, he had an apartment, bought a pickup truck, and saved $5000. His story is just one anecdote, but it is an interesting one.
http://www.nevblog.com/category/homeless-experiment/