What constitutes a "hobo." Does one have to be "financially challenged" to qualify? Does one have to have an "off the grid/screw the mainstream world" mentality, ride a Wal Mart bike with panniers made out of Tupperware and depend on the kindness of strangers for some of their sustinance?
The reason that I ask is that in a campground in Sevilla I met a couple who had been on tour for over a year on a couple fo continents. IIRC, they were from Phoenix, and the husband once owned a bike shop, which he had sold. They had come to Sevilla to "sit down," as they called it, which meant taking a month or so off from riding. They were planning on renting an apartment. That and a couple of other things, including the fact that they had custom Robert Beckman racks and panniers and a custom made tent, suggested that money wasn't a pressing concern.
They didn't seem at all like some "fascinating subspecies" who were part of some "subculture," but rather two successful adults doing what they enjoyed. I saw them as two people who liked to explore the work on bikes are were fortunate enough to be able to do it long term.