Now, I have started Rolling Nowhere, by Ted Conover. He is one of my favorites and this was his first book. Conover preceded Morgan Spurlock (Super Size Me, 30 Days) and pioneered the non-fiction genre of living the subject matter. Conover traveled with illegals and crossed into the U.S. in Coyotes and became a prison guard at Sing Sing for a year in Newjack.
In Rolling Nowhere (1984), Conover hopped on trains all over the West in order to write about the American Hobo.