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Well, skizziks, there's two things to think about for your situation.
A: Do you have the economy to live the drifter lifestyle forever? From what I know, you don't have any income and have steady (if miniscule) expenses. At some point you'll have to get some income, and that could provide ties to an area.
B: I do think that it could get lonely, and that there's some people who it'd work for, and some it wouldn't. I could never do what you're doing for an extended amount of time, money or no. I need human warmth. With a partner? Sure.
I also don't think you have to keep this lifestyle forever. At some point I hope you'll have your fill and reevaluate what you want to do with the rest of your life, and then hop back on track to achieving it. But that's from my biased perspective: you should (and will) do what you want.
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