I travel the world country hopping every month or so and stay almost exclusively in places sourced off airbnb or wikitravel. Works fine, I don't know if I'd qualify as an outlaw wanderer? Perhaps not.
Or you could buy an RV and travel whatever land mass you're stuck in, or you could buy a yacht and travel the seas, or the options are fairly limitless. Buying a house and settling down is just the path most frequently taken, not the only one by any stretch of the imagination.
AirBNB (and hotels in general) are still renting. sure, short-term renting, but you are still renting a residence, even if it's for a day.
Note, by 'outlaw' I did not mean "breaker of the law," I mean "not materially protected by the law" (or, more correctly, protected less by the law.)
If you don't have a place to keep your stuff, well, you aren't going to receive the same protection for that stuff as someone who does. You also aren't going to receive the same level of personal protection against, e.g., harassment that you would in your own space.
Property protection is amusingly tenuous when you expand the playing field to the entire globe. In my opinion; live minimalist and have insurance for what you have. Has worked for me through Vietnam and Thailand and I am about to try Cambodia.
Or you could buy an RV and travel whatever land mass you're stuck in, or you could buy a yacht and travel the seas, or the options are fairly limitless. Buying a house and settling down is just the path most frequently taken, not the only one by any stretch of the imagination.