Pretext: I am 22, I make good money, own a house in the city, and do some mid- distance multi day backpacking about 2 times a month for 2/3 days each. I live in the USA.
I want to be homeless (at least for semi extended periods of time) and travel on the cheap. I am a dual citizen in the EU. I want to quit my job and sell my house and use the money to travel - I want to try hopping trains once or twice to see if I hate it. I really want to try going to northern india or former soviet bloc states. It's all I can think about. I think if I liquidated all my belongings and maybe worked for a few more months I could walk away with 100k cash.
Should I do this? Is this a grass is always greener situation? Why is my current success not enough for me.
Pic related, it is a picture I took when I was /out/ pretty fun time.