I recently re-read On The Road and Kerouac, with all his romanticism, came of as a bit of a ****** - he 'freeloaded' quite a bit and yes, he did some tough jobs, but whenever he reached a dead end he'd either wire his aunt in NY and ask for money and/or go back to NY to live with her. IMO, real hobos have no fallback and must rely on their own achievements.

Probably more difficult to find random, short-term work these days; though might be easier on the internet if you have those skills. There's that whole #vanlife movement, so I suppose that's a bit 'hobo' or nomadic. I have heard of a guy who went on a long bike tour and loved it so much he was still touring the world 3 years later.