Homelessness how-to?
Not to join in the pile-on, but what you’re talking about isn’t really homelessness, it’s slumming or bumming about. Which is fine, really. I’ve been homeless and I’ve slummed it. Slumming is fun because at any time you can stop. Being homeless sucks because you have no idea when or if it will end; you have very little control of anything in your life, even if you’ve managed to avoid the classic pitfalls like addiction and mental illness. I was “working homeless” for six months, and it’s not something I’ll be forgetting any time soon. That said, if you decide to bum around the country or even just a particular city, the advice at Survival Guide to Homelessness (mentioned by jessamyn above) is really good. I wish I’d had access to it when I was down-and-out.