As someone who's been homeless, I have to say rural, but with access to a town. Why? Fucking city hobos/street trash will fuck you up and steal your shit more often in an urban environment, because there are simply more of them. Also, harassment by police tends to be more intense, depending on what state/city you're in. I will say it's pretty easy to be homeless in New Orleans because you can sort of fall into a clique of homeless kids, land squats, get a dish washing job really easy and rent a place in 9th ward that's just above a squat. Also food stamps come quickly there.