I would give it some serious thought.
Maybe get a pack and blanket and camp out a few nights in your neighborhood or back yard just to see if it's even something you can tolerate, most find fairly quickly that it's not for them.
There are ways to live the life without jumping right into the aspects of it which have a tendency to eat people alive. For example, I am not formally employed, but I have a decent amount of money saved away, I have a fairly nice house, and I have accumulated a good deal of material possessions, but it has not turned me into a money driven materialist, and honestly, avoidance of these perceived Bourgeois trappings that seem to be bother you is more of a psychological issue than it is a physical one.
When I was around your age, perhaps a few years younger, I played in a touring band, eventually I lost control, was partying really hard, and got into some legal trouble for trashing a fast food restaurant, I got put on probation. After 8 months they let me go, and I just took to the street, I was only 16 but I had friends from coast to coast from playing in the band. I had already been sleeping outside a good deal since I was a kid, drunken abusive parent would kick me out, then i was living with punk rockers, so squatting and traveling came naturally. I guess I have always had a high affinity for owning very little, moving frequently, and never settling. ...I swear if I stay in the same place to long I loose my fucking mind. Plus, I green up reading Kerouac and the beat writers, and was raised around "hippies", so it was easy to romanticize and rationalize what I was doing...
Now due to a medical issue I'm stuck.
Honestly, the majority of your trappings are in your mind, seek mental freedom and physical freedom seems far less relevant.
Have you thought about going backpacking through europe, or taking a cross country trip in your car? Something like that, where you can have your adventure then return?
When I was your age I wouldn't listen to anybody, and I can somewhat understand your desire to get rid of everything you own and hit the road, but for the love of God be careful!
...even when you leave with a road-dog there are going to be long stretches of time when that person is separated from you, you need to know how to take care of yourself, trust me, you can't be dependant on others in that situation, it's a recipe for disaster.
...any way, be careful, be smart, don't trust anyone, specially those who are to eager to be your friend. Be a good judge of character, and use your head.
