This question originally appeared on Quora. 
By Michael Forrest Jones
I've been there. Some years ago, I actually lived out of a van for the better part of a year.
You don't really save any money. It's the little things you take for granted that, once you don't have your own kitchen or bath to walk into and get them anytime you want, suddenly become individual expense items; that all add up to get you.
I brew a pot of coffee every morning (it's the only thing that gets me fully awake within forty-five minutes of getting out of bed): a big $10 can of Folger's lasts me 2-3 weeks. Go to a convenience store and buy it every time you want a cup, it's a couple bucks. You want to freshen up at home, there's the shower. If you're living in a van and it's time to do just that, plan on $15-20 at a truck stop. Over the course of a month, all the little things that there are suddenly prices on add up to enough that the money would have been better spent to rent something, even if all you can manage is an acquaintance who's having his or her own problems with the bills and is willing to let you crash on the couch for fifty bucks a week.
No one can afford to eat out every meal, even at Burger King. Canned stuff from the supermarket isn't really good (especially if you can keep only things that require no refrigeration other than an ice chest - if you can afford ice - and have to eat everything uncooked), and it doesn't provide a balanced diet. If you're living out of a vehicle, you're always burning gas whether you're going anywhere or not (you need the heat in the winter or the a/c in the summer); and back when I did it, gas was much cheaper.
Unless you're making enough money that the idea of trying homelessness to save costs is too silly to even consider, you're going to be too distracted by day-to-day survival and maintenance to even dream about VC's. And believe me, they think things about anyone who makes less than $30k a year (if you're that valuable, why can't you command a bigger salary than that?). Funding some venture proposed by a homeless guy is not the kind of day's work that a VC is going to want to tell too many people about back at the club.
Just being homeless is going to draw the wrong kind of attention to you: there's not quite the sympathy for 'the homeless' that there was twenty years ago when the problem first started drawing public awareness; and when the local cops pick up on who you are, they're going to consider you a continual subject of interest. (A friend's wife was aghast that I told her I got stopped and checked out by the cops a couple times a week, like I must be some sort of cockroach. I told her, half by way of reassurance and half sarcastically, "well, if it makes you feel any better, I'm not wanted for anything...") I was paying off accumulated parking and 'defective equipment' tickets for six months after I eventually resettled - and succeeded in paying them off that soon only because a lawyer friend appeared in court with me (that's how bad the total accumulation, and delinquency, had eventually gotten) and worked out a deal to reduce the total amount. (That one even had me living in the van again for a few days, a couple months after I had a place. A Pennsylvania constable had a warrant and was all hot to put the clinker on me over it, knew where I was living; and I had to spend a few nights across the river in Jersey to stay clear of him - or at least out of his jurisdiction - until my lawyer could get back from his beach trip and straighten it out. It was either that or the county jail.)
Any good sized town is going to have a couple of soup kitchens, but the worst thing you can do is spend a lot of time around other homeless people. (There are several reasons, some psychological; but the big one is that, as bad off as you are, you're probably well off by contrast to most of the others, and ... things level). Your survival and comfort depends on being the kind of homeless person that people ignore - that people can ignore. (We feel ashamed of ourselves because of the fact that we go to church and worship a homeless man on Sunday, then look down upon and go out of our way to ignore homeless people the rest of the week; but really, being anonymous in a situation when you're homeless often has its advantages. You'll notice right away: even people you thought were your friends will start treating you differently.) You want to be able to sit next to someone in a diner and never have that person suspect they're sitting next to, and probably chatting with, a homeless person.
(Some people, if they do find out, try to reach out and help in various ways; but some people think things about you. You have to be discreet about who - for lack of a better word - you 'come out' to. Remember my friend's wife a couple paragraphs back? Months after I met this guy and we became friends - he was one of those that found out and reached out - and even after I'd resettled into a fixed place, she was still just a little uncomfortable around me. I suspect people think, 'what kind of guy would get himself into a fix like that?' and - especially if the answer isn't obvious, like a drinking or drug problem - let their imagination run wild and come up with possibilities that are even worse.)
You'd probably draw even more of the wrong kind of attention to yourself if you do 'homeless person' things: letting your personal hygiene and grooming get too bad (hello, once again, Flying J Truck Stop, another twenty bucks... ); panhandling (fortunately, I had a couple of part time jobs and never got quite that bad off), drinking (if you want a beer at home, there's the refrigerator; if you're living in a vehicle, better not let the cops drive up and see you), being too obvious, or too obviously trying to avoid attention. If you meet a nice girl (and it's not easy to get nice girls to take an interest if you have no fixed place of residence), better hope she's got a place; only teenagers steam up the windows in parked vehicles.
There are hacks you can learn. Some of them are crude. I have stripped down to a pair of swimming trunks, headed to the car wash, and made sure I got scrubbed down as good as the vehicle did - at 3am (hey, save the stop at the truck stop and the fifteen bucks) - but any other time of the day or night, anyone who sees you doing that is going to think things about you. Buying a thermos from Wal-Mart, then filling it the night before at a convenience store cut my coffee costs by about a third and made the routine of getting up in the morning much more comfortable. Best places to park for the night: shopping centers with a large parking lot, but neither a spot where there are lots of passerby, nor in too isolated a corner of it (in either case, you increase your likelihood of getting attention and being checked out). Church parking lots tend to be left alone; as are the people in them, even if they're spotted by a pastor or a member of the church staff, so long as their behavior isn't objectionable - and so long as it isn't your own church. (Like I noted earlier about people you thought were your friends; before that year was over, I ended up finding another church. Despite the fact that I'd attended that church for several years and most people there should have known me, a small but growing number of them made me feel about as welcome there as a recently-paroled serial offender.) The end of a dead-end street in a developing industrial park frequently worked well for me: it was isolated, I could let the cat wander around outside, and the township cops checked me out a few times when they saw me there, but generally left me be. So did a truck stop in Jersey: it usually has a parking lot full of people sleeping in vehicles that aren't designed to be lived in.
'Public' parks and park and ride lots do not work well, rest areas and recreation areas work only if you have out-of-state plates: such things are expected at a certain level by people traveling on a low budget. (On a return trip from North Carolina, I did spend one night in the middle of Chesapeake Bay, on one of the islands of the Chesapeake Bay Bridge-Tunnel.) Stay away from the middle of town, period: you're not one of those homeless people. Besides, one of the few actual benefits of being a homeless person is that you can afford to live anywhere you want - almost, so long as you're discreet. Residential neighborhoods are problematic: ideally, you'd want one where people park on the street and where no one ever looks out the window, then the question becomes, should you want to be in such a neighborhood?
It's politically incorrect and insensitive to be harsh on homeless people, but the practical reality is, you don't want to be one. If you're on private property, the cops run you off; if you're in a public vehicular area, you're loitering and they'll still roust you if they spot you. Like the Swedish sociologist Gunnar Myrdal noted about African-Americans in his Nobel Prize-winning study back in the 1940s, in the winding-down days of Jim Crow prior to the civil rights era; you become part of a class of people that the rest of the country would like to just have disappear in its entirety, if they could think of a socially or morally acceptable means of making them all just vanish ... There's no significant cost savings involved in homelessness, and any savings that you do realize have their own costs.
It's doable, and survivable, but not really worth it. It's not all bad: it actually has its positive points. I focused here on the costs, because that was the question. It would get old from time to time (a Dodge Caravan has adequate space, but isn't exactly designed to be lived in!), but it wasn't a complete downer. Starting out, it was a little scary, but it dawned on me the first night: this isn't a problem, just remember the stuff you learned in Scouts when you were a kid and use common sense. Many people live in six-figure houses and sweat out a mortgage they can't afford: this van isn't much, but it's mine and it's paid for - I may be 'homeless,' but I'm a homeowner now!. The worst that can happen is someone can come along and tell me to move it: fine, I'll butt out. I was amazed and delighted at how well my cat, Ralph, took to it: much better than you'd think can be expected of a cat. He was a little skittish at first about riding in a vehicle, as any cat would be, but he took right to being fed, living day to day in the van, and moving around all the time; so long as I made an occasional 'liberty call', took him somewhere where I could safely let him out and gave him some run-around time, and let him do 'cat things' for an hour or so. He always came back: he knew that wherever we might be, even if it was a hundred miles away from the last spot, that van was his 'home.' One of my favorite activities was, and still is, a road trip: during this particular year, I had a job that required travel around the whole of eastern Pennsylvania and parts of Jersey, and recreational travel was easy: I was already packed, and using up gas anyway. (I could have probably resettled sooner than I eventually did, but every time I got ahead a few bucks, I was running back and forth to North Carolina because of a family issue.) Even now, if I were of more modest means and had to choose between overpaying rent to a slumlord for a too-small, cheap, crummy place in a bad neighborhood; or living in a minivan, I'd take the van, without hesitation.
If I did have it to do over again, I'd prefer to do it with a 28-foot, class C motorhome. But then I'd be driving a gas hog that would use up enough fuel to wipe out the savings. No matter how you slice it, any cost savings will have ... a cost.