The key to being successful in this kind of urban camping is to find a spot invisible from roads or paths, with an inconspicuous entrance and/or exit, and to be discreet in how you behave there. For example, fires are probably not a good idea in most cities but Sterno works fine if you need to cook something.
Squatting is a very different situation. In most American places they can bust you for breaking and entering if you take up residence in an abandoned building. In parts of Europe, the laws are different. Know the law before you squat. While hitching in the Southwest, I used to scout out houses for sale as I walked an hour or so before sunset. If you can find one you are pretty sure is not occupied it’s usually pretty easy to return after dark and jimmy open a back door or window. Older, run down houses usually don’t have security. If breaking in to the house is too risky, you can usually find a porch, shed, or garage to get you out of sight and the elements. I’m not advocating you break the law, but if you are in need of shelter, this is one option.
We spend one third of our lives in bed. We use our beds for sleep, romance, reading, and recovering when we are sick. If you have a bed, be very glad. If you don’t have a regular bed, here are a few options to get one.
The Bedroll. I’ve had lots of bedrolls. The basic bedroll is a tarp or groundcloth laid out flat, a wool blanket over that (or two if you are in the cold), and a foam pad on that. Fold the blankets and tarp around the pad, and roll it up. Unroll it when you have a good place to sleep.
If you have the space, the tri-fold cushions you can get at Walmart make great beds. Cushions of any sort can be great to sleep on. Foam is good but it collects moisture and can get heavy and cold. My favorite simple bed is a Thermarest. It has a self inflating bladder, rolls up small, and can be folded into a decent chair.
I believe sheets are important. I highly recommend sheets. The higher the thread count the softer the sheets. Soft sheets can make an uncomfortable bed feel wonderful. Same goes for pillows. Crappy pillows can cause a bad nights sleep on a million dollar bed.
Makeshift Bedding. Old curtains or material can easily be made into a blanket. The ideal size is at least 60” wide by 2 yards. I like to sew a footbox into the bottom. Heavy-duty 33-gallon garbage bags can be used to make a ground cloth, a poncho, or a small tent. Large ziplock bags filled with air make good pillows. A bunch of them makes a decent air mattress.
If you plan on living in your vehicle there are a few things to take into consideration. First, make sure you can sleep comfortably in it. Pickups with camper shells, vans, and station wagons are your best bet. Second, make sure the vehicle is legal so you don’t get your home put in an impound yard. Third, pick your parking spaces carefully. I’ve found parking in secluded areas is almost always a mistake.
The best places to park are places where there are people around and plenty of vehicles moving in and out all the time. I’ve parked in dead ends and had people report me to the police because it was "suspicious" to see a car parked there. Oddly, I’ve parked in residential neighborhoods where I didn’t know a soul for weeks on end and no one thought anything of it. I suppose they all thought I knew someone they didn’t know.
The best places to park are where you have friends. My friends in Seattle allowed me to park behind their house for months. It made them feel secure because my being there discouraged the local druggies from congregating and doing deals in the alley. I did yard work and helped out around the house to keep things nice for them and me.
I’ve lived in three different VW buses in Alaska, Washington, Oregon, and Hawaii. In every case, not having to pay rent allowed me to live alife I otherwise wouldn’t have been able to afford. With the money I saved on rent I was able to purchase airline tickets, train tickets, or able to go out on good benders now and then without a care.
Maintenance. If you live in your vehicle, you better pay attention to the maintenance. This includes oil, brakes, and tune ups. It also includes keeping your tags current, your headlights good, and your insurance card up to date.
Legalities. Laws vary from place to place. On Oahu, it is illegal to sleep in your vehicle from 6 PM to 6 AM. They call it habitation. The fine is larger than the fine for sleeping in the park. Know what the peculiar legalities are for where you are.
Localism. There are some places that you don’t want to be. Parking in some neighborhoods is just plain dangerous. Not only might you wake up without your tires, you might not wake up at all. Know where you are parking.
Sleeping In. Sleeping in can be a problem when you live in your car. Think about where you are before you go to bed. Otherwise, you might wake up to a surprise. If you are parked in front of an elementary school it may be quiet at night, but what about when the kids arrive. The urban street might seem quiet until the disco opens at 10 PM. One night, I went to sleep next to the remote control car racetrack. I woke up early.
Gas. Gas is expensive these days. The funny thing is, it can vary a lot in a short distance. There was a difference of 18 cents a gallon at two stations less than a mile from each other a few days ago. Try to save on gas. One good way to do this is to use the city bus if you find a good parking spot.
Getting Comfortable. Each car is going to be different. It’s not so hard for me to live in a car as I’m not a huge guy at five foot seven. Larger folks will have to figure out how to be comfortable if they want to live in their cars. Make sure you have space to move in your vehicle.
Being Inconspicuous. If you want to attract attention you can do it lots of ways. You can hang towels and sheets in the windows of your car, you can pee in people’s front yards, you can throw garbage around your spot. I prefer to be inconspicuous. I don’t’ have too much stuff. I made curtains for my van that look normal, I use parks and libraries for their free public restrooms, and I put my garbage in trash cans. Even though I usually slept during the illegal hours on Oahu for months on end, I never got pegged.
Drinking Booze. I like to drink once in a while. You have to be careful about it though. Especially when you live in a vehicle. Only drink when you know that you won’t need to move the vehicle. Never, put the keys in the ignition when you are drunk. This is not only to keep you from drunk driving, it is also to keep you from getting a needless ticket. Even if you only plan to listen to the radio and go to sleep in the back, a police officer can give you a DUI if the keys are in the ignition and you are drunk. Besides that, don’t drink and drive. It’s a good way to end up dead or in prison. There are better ways to kill or incarcerate yourself.
Cooking and Eating. I like to barbecue in the park. I make coffee on a single burner propane stove in the back of my van each morning. I’m discreet about it. I don’t think anyone sees me cooking in the van. If I go to parks, I cook at the picnic tables. No one seems to notice or care.
Living in vehicles can be fun, cheap and easy. I estimate that with insurance and gas it cost me about $100 a month to live in my van on Oahu. Much less than the $800 or higher most of my friends pay for rooms or apartments. Living in the Pacific Northwest was even cheaper.
I’ve never been a rich man though I’d like to be someday. Maybe you figured that out by now. Because of that, I’ve never owned a new car. They’re too expensive. I see the price of a new car and I remember that my parents bought a house for that same price back in the 1970’s. Lot’s of people never own new cars. That’s okay, because there are plenty of decent cars out there that are dirt cheap.