This is a pretty bougie version of the traveling life. I bikepack and packpack, and I live in the city and talk to interesting people. There are still rail riding adventurers, including the Crunchy Punks and a lot of men traveling around on bicycles. I've shared campgrounds, coffee, weed, and even road-kill jerky with them. The crunchies are usually dressed in black or camo, and have a guitar and a dog. They'll busk and panhandle, and include a surprising number of young women. The bike hoboes are usually pulling a trailer and kind of drifting from town to town. Yes, they have smartphones and know how to connect to wi-fi. They all party pretty hard, but don't call them "homeless", and generally they hold the homeless in contempt. They are traveling. They all have some great tales to tell, but the Why am I living in a tent? story usually involves a woman.