In the book, "A Treasury of Railroad Folklore" there is a chapter on hobos, etc. There were different classes of them. The higher class ones simply liked the life of a vagabond, travelling from place to place for the fun of it. Although they sometimes stole (usually chickens
), most would work for food and shelter before moving on. OTOH, there were those who had definite problems, just as many of today's homeless do. So far as hobos and the railroads are concerned, I would imagine it is much harder to "nail a drag" than in the 20th Century. The configuration of modern equipment probably makes it tough. In addition, there may be means of surveilance of passing trains that make it harder to hop a freight.
I don't have photos, but just outside of "Galesburg", on my "Grashhook, Galesburg & Western Division of the Burlington Route, there is a hobo jungle, with several 'bo's resting around a campfire, hoping the "bulls" (railroad detectives) won't see them! Of course, on my railroad, the "bulls" are instructed to be as gentle as the actions of the knights of the road will let them be, mostly just telling them to move on from railroad property!
A few blocks away, in the alley behind the main drag of Galesburg, there are a bunch of "gentlemen" kneeling in a group. One has his hand in the air, and appears to be shaking it, prior to throwing some small objects against the wall! Around the corner, a traffic cop is obviously unaware of these scofflaws!