Well, if there are people using the place, I'd say they're more likely to be hermitic squatters than homeless drifters.A very long distance and yea, I've watched several train hopping vids. They are definitely modernizing train hopping with Youtube.
I do remember reading an article about a "sport" called something like extreme freestyle hiking. They can be on the trail for months, often alone. Some prefer to avoid others totally and live off the land. There were a few stories about hikers taking "liberties" for a place to sleep or something to eat, like letting themselves in barns, shed, abandoned homes, etc. You'd think these folks would have maps/GPS data sharing of isolated places to bed down, certainly something more advanced than hobo symbology.