The RV lifestyle sounds like it could be fun. That's something I've been fascinated with ever since I was a little kid. And when I was 12, my grandparents took me on a 6-week cross-country camping trip, and that was one of the best memories of my childhood. We did it pretty cheaply, too. 1976 GMC crew-cab pickup with a 10-foot SKAMPER slide-in camper. It had no bathroom in it, and Granddad had pulled out the water tanks for more storage, so the only time we even had water was when we were at a campsite with a water hookup. We had electric (if the campsite offered it) and propane for the stove (I think the little refrigerator could run off propane if you didn't have electric...or maybe it just ran off the truck's battery, I can't remember), and that was about it. But we had a blast. When you're always travelling like that though, 24/7/365, where do you get your mail sent? What would you use as a mailing address?
I don't know if I could deal with that Gilligan's Island approach, though. Even though it's dirt-cheap, I think I'd just get bored after awhile. But then, I guess your roots wouldn't be all that firmly planted, so if you got bored of one area you could just pick up and build a new grass hut near the next coconut grove you find.