I crashed for free in a trailer park for a year or so during college. Was a good move, looking back. Nothing was more fun than walking around with a crew of armed old vets kicking out illegals and homeless riffraff who made there way into our park.
I'm talking about being truely homeless.
For me, I was living in a van for 3 months. I'd drive to different spots, park the van and sleep in it. Usually stay in each town for 3-6 days then drive on the the next town. I slowly made my way from San Francisco to Seattle like that.
I sold the van in Seattle because the transmission was fucked up. And then I was just 100% homeless. Walking around with the big backpack, hitchhiking sometimes, hooking up with crazy hippies and crust punks and getting rides with them, etc.
For a while I was living in the deep forests of Oregon and was basically living like a tribesman. It was just awesome. I didn't miss any of the material comforts I left behind.
I told my family that I moved to Portland Or, and got a job out there. Because if I told them I was wandering around homeless they might not appreciate it to much.
I miss it. After getting back into the rat race again. I miss it a lot.