Back in the '30s lots of out of work guys and others who just wanted avoid it did just that. There was a fellow on my mother's side of the family, one of her aunts' husbands who lost his job, left his family, and hit the rails. He hoboed arround and never came back. Until about 40 years later. Just showed up one day and knocked on her door. She had remarried and her second husband had died leaving her an elderly widow. The old hobo may have wanted forgiveness, I'm not sure. And I don't know if he got it. All I know is he didn't come back around after that.
There are plenty of songs about hobos. Most of them romanticize the life. Some of them offer insights. Hank Snow's "Crack in the Boxcar Door" is a romanticized view of the freedom that the rambling hobos were said to enjoy.
Jimmy Rodgers "Hobo's Meditation," is still a bit romanticized but does provide the listener with some insights into hobo psychology. I especially like the line..."will we have to work for a living...?"