Maybe there's more than one version of homeless?
I lived what I would call semi-nomadic for about 5 or 6 years in Northern Az about 25 years ago. I spent an average of 10 months/yr camping, under the stars, on my motorcycle, and truck camping, and had a tipi I lived in for a couple years off and on. I was mostly camping on National Forest land, and moved around a lot. Never had a problem with the Forest Service. I guess the time I had my tipi on my own land I wasn't exactly homeless. Rabbits were in season 12 months of the year, and I loved hunting them. I worked part time, roamed a lot, shot a lot, and had a blast. I don't want to do it again at this point, but could if I had to. I certainly wouldnt be anywhere near a city.
Back on topic, I mostly carried a 4" Smith 29, with some flirtations with a couple Colt SAA's, a Colt 1911 or two, and a few Rugers. Always had various guns in my rig, pistols and rifles. So far as I know, there isnt any law against having a gun anywhere I've been, so no reason to be concerned about the law. I had an address, a friend let me use his for my paperwork that required a physical address, and I had a PO box for my mail, much like many retired people do when they RV for their retirement. I think I could comfortably do the RV thing, but I reckon that isnt really homeless, just a home thats not fixed in one spot.