I have briefly hung out with some of the homeless folks that I met mostly on the Pacific Coast route. In some cases there was a thin line between homeless guy on a bike and bike tourist. Some of them had nice gear, but were definitely homeless. Then there were others that didn't meet the definition of homeless that folks typically use, but who had chosen to sell their home to go on tour for a year or two.

One guy I met was "walking across the US" pushing his gear in a big double wide baby jogger. He had started in 2005 and in 1012 he still had a good ways to go. He said that at some point he decided it wasn't about the destination. He stopped for a week or six months when he felt like it. He had a social security check every month, a debit card, and a lot of nice gear. He used his daughters address for mail. I'd say he qualified as homeless by just about any definition. He liked the food at the Apache Gold Casino so he had been staying in their campground for weeks. I had a couple meals with him in the casino. He treated me to dinner and I bought him a meal the next day. He seemed happy to have someone to talk to for a change. He was a nice guy and interesting to talk to.