Here’s a video that happened to come up on my YouTube feed today. It’s by someone doing what I’ve always thought of as the quintessential hobo activity: hopping a freight train. Beautiful scenery.
I suggest to look up his trip up from Mexico, following the migrant route. For a different view of the same trip, his travelling companion (automous something) has his own channel.
RanOutOnARail isn't really a hobo though ... I think he's a software engineer in Texas somewhere.
Hobo Shoestring has an interesting channel also, albeit with a home base. You'll learn a lot about trains, and hobos' most hated adversaries, the 'homebums'. :D
And of course, there's a 10x hobo, in stobe-the-hobo (RIP), well worth watching all his videos.
Love Shiey and he also goes on quite a few trips with this guy (https://www.youtube.com/channel/UC8iPVSFr42KUFf8DKsmnvSw) who is very well educated and more philosophical and artistic than Shiey. Like them both a lot, but they're different flavors of the same genre.
https://youtube.com/watch?v=xlPWF8LFXS0