grecy, what sort of vehicle did you do your trip in? Did you sleep in your vehicle, a tent, or what?

I'm trying to figure out how I could do something similar. I may not like it so I want to start with a short trip.

I still can't figure a way around the health insurance aspect though. In the USA, life seems to get incredibly difficult without a permanent residence - health insurance is not possible without it, so far as I know. And a driver's license probably gets tricky as well. I don't want to take a nice trip and wind up either in jail or facing a huge debt burden due to some unexpected health problem.

I realize you don't have the health insurance issue since you've already mentioned that you live in a country (Canada?) where this is not an issue.