This is an interesting thread/question to me. I never got as "fully" into traveler lifestyle as many here, (so far!) but I have been houseless on and off at times, and after I left my home state, the next handful of places I lived didn't really "take," not even as bases to return to between travels.
What I did was farm-hop, WWOOF for a while, hitchhiked back across the country, up & down the eastern US for a while, get confident that I could live outside without money in different towns, and picked up various day labor... Now, some places I was an obvious outsider in more insular or marginalized cultures and couldn't synch up with them enough to feel I was getting any social 'return' from my energy. And one place I tried to participate in, well, not the mainstream society, but cultural scenes that were not explicitly political, and got hit with a whole lot more bigotry and exploitive behavior and far less people with any critique of it, which is frustrating when wanting to feel I can connect with people outside smaller radical/political settings. And some places I passed by and caught glimpses of people and projects that called to me but I just couldn't get a foothold...
So I wound up where I am by chance, and was able to do life stuff here that I'd tried and failed to do elsewhere. I care about being places long enough to learn the landscape, about the animal migrations, what medicinal plants grow there. I want to both develop better outdoor-living skills & "marketable" work skills, and I've picked up some construction/remodeling/woodworking experience here that I hope can also carry over into mutual aid / autonomous infrastructure settings. (I'm also not complaining about just doing kitchen work in a warm building when winter set in...) Producing things for direct human use, not for market-exchanges! To some degree I can already do that, in both more organized and ad-hoc community networks. To be stable enough to *modulate* my interactions with people, to engage or withdraw as is harm-reducing in the moment - saw enough need for this in spaces where people were all trying to look out for each other and defend their people from [mining companies, police brutality, drug pushers, whatever], but nobody had enough resources between them to get any space from each other.
Like my goal above all, back in the day of getting the hell out of high school and my hometown, was to make a life with people who wouldn't encourage me to be a sociopath, and/or enable more abuse against me, as the Combine wants us to do. But, right, "getting the knife out of my back" is not a hobby, I just wasn't really far-enough up my own hierarchy of needs to have other interests. It's been hard to make my way to places in life where I *can* think beyond that.
So - preferably I can take care of myself, with money or without, well enough not to create needless emergencies for other precarious people. Ideally I could earn enough income to provide for emergency relief for fellow travelers, but there are other ways to get better at that besides having money. So - can I find enough people in a given place who share my goals/ethics, enough that I can run things by them when I'm trying to get *other* stuff done with people who are all over the political spectrum?
Beyond that - proximity to the ocean and/or clean bodies of fresh water.