like you noted, i'm more free daily than a good portion of people in the world. The most free i've felt though was last summer backpacking around NC/SC with my friend. Outside of seeing our friend and a music festival we had no set plans, so everyday was just about finding something interesting to do and finding a dry place to sleep that night.
How old are you? Just curious, because if I tried that kind of stuff now I would probably end up getting arrested. Ex. When my parents were dating, if they wanted to go camping they took a tent, found a nice spot in the woods on the side of the road or on the beach (Upper Peninsula of Michigan, Mid-late 70's) and camped. Can't do that now.
I just turned 21 a few month ago, so pretty young. Most the places we slept outside were around the area of the Appalachian trail so i think they were pretty used to back packers. Sleeping in asheville we were in between some bushes and a building to avoid the rain so no one could really see us anyways. I don't think you'd get arrested though! It's not illegal to be homeless, they'd just tell you to move along elsewhere.