I gotta say that house-free living in a major city is certainly has its own advantages: if you're struggling too hard to survive, you're probably doing it wrong. I've been extraordinarily poor, while living in a city—and not even a world-class city such as London—and very rarely had to pay a cent for food: I wasn't even hitting up every source in the area.
Don't even get me
started on hiding-spots!
The trick I've found is that I only really lose faith in alternative living when around folk that were staunchly against the very notion. When about town, left to my own devices, house-freedom wasn't much a scare at all. My only worry was computer-access, and I've since addressed that. But being around depressing people depressed
me, thus my current endeavor to stay away from them for as long a daily period as I'm able. (Current record? 14 hours! I can't wait to go for more.)
My concern is still food. I need more sources. Two beats one; but six beats that, eh? Wednesdays and Sundays are basically set in stone. A stretch beyond a stone's throw lies a couple houses I've yet to investigate: their mailboxes have been properly recorded, thankfully. The weather's turned a tad frigid, so my movement may do a great spell better than its usual: even as a native Floridian, I am utterly enamored with the cold.
With the last of my funds, I can stay bathed for quite some time. Recently, I was struck with the idea of washing clothes by massaging them with soap while wearing them: from there, a quick swim would easily rinse 'em. Being in a water-side town isn't too shabby. I still loathe the abundance of horseshoe-crabs in the waters.