being homeless doesn't have to mean sleeping outside, unprotected from the elements.. though i tend to prefer it, at least the outside part. there are many options, more or less depending on your comfort level.
this is where it comes in handy to be real resourceful. hanging around my hometown i could always hit up homies or family for some couch time, back yards to camp, maybe even an immobilized vehicle to inhabit. there's also a sun room i can slip into if i don't find shelter elsewhere.
unless you have some homies that like to collect bohemians on their property, depending on the kindness of others can only go so far. i prefer only to use these resources when i cannot find shelter for myself, or weather conditions are unreasonable for sleeping outside.
i personally am uncomfortable in homeless shelters. i feel safer finding my own sleeping space, and less anxious if i am free to come and go as i please. i have tried in the past both winter overnight shelters and women's shelters, both i find too stressful. good thing there are other options..
of course, there's always tarps and tents. this is the best option in my opinion, finding a lightweight solo shelter at a backpacking equipment outlet could be one of the best investments you ever make. for well under the cost of a month's rent, i have found sufficient lightweight shelters for one person or two. less is more when you carry around everything you own, so finding the lightest shelter with the least amount of parts is key. if you have storage somewhere and the capability to leave behind things you don't need immediately, then finding a 2 pound tent instead of a one pound tarp shelter will be worth the extra little bit of weight.
tresspassing is illegal, so finding some private property that i have permission to camp out on, that's fantastic! if not, i make sure practise well my stealth camping skills, leave no trace of my presence, and refrain from getting caught. there's plenty of places on outskirts of cities that are still within walking distance of public transit where you can find a spot to set a shelter. parks, along hiking trails, back acres of farm property [beware the dangers of trespassing], anywhere your shelter can be set up unseen.
finding a shelter
i think one of my favourite places i have ever found shelter was in a garden shed in Nova Scotia. the inside was finished with scrap paneling and insulation ripped out from the basement, a table and a couple chairs, an oil lamp and a real comfy hammock. it was an old hand built shed with a window along the whole one side of the shed, and moss covered wooden shingles on the other side.
in a bigger city, concrete jungle so to speak, there's many nooks and crannys to hide out in. i've found some pretty sweet overhangs to hang out under in toronto, usually covered back entrances to big businesses that don't get used during the night. this eliminates the need for a shelter. also check out parking garages, go up a few floors and you will find the platforms between staircases to be a good spot. on cold nights you could hang out in a bank lobby. i'd only do this in desperation however, i try to find places unseen to avoid getting robbed. i don't like to spend too much time sleeping in the concrete jungle. i find the dangers posed by other humans much more threatening than possible dangers posed by nature.
to the van!
there's another popular option, living in a vehicle. i personally have zero experience with this, besides a couple months i lived in a camper with my dad while he was building a house. if you would like to check out a blog dedicated to this style, see The Guide to Homelessness in my Links. i do have one tidbit of information.. if you live in a van or a camper, all Wal-Marts in north america allow one consecutive night parking in their lot, free of charge and fear of parking enforcement. many of their stores in the states are open 24 hours, and this is a way to attract more business, and clients in their slow hours. the nights are a perfect time to take advantage of the public restrooms to get clean.
the homeless lifestyle has such a broad spectrum of styles within itself, and truly the options are endless. one could travel for months at a time just surfing couches from town to town. there's handy resources online, like one of the world's biggest online traveller's network, CouchSurfing.org.. there's literally hundreds of thousands of couches available. there's a registration process, and users leave their feedback about their experiences with each other. it's about as safe as the interweb could get. i've heard many positive stories about others using this site, and it's certainly one of the most handy resources i have come across online to date. and then there's facebook, the one stop shop WalMart of the internet world.. everyone and their grandmother has facebook these days. you never know when a status message will find you connections for places to stay in your city or abroad, and sometimes from people you would have never expected.