Boy, I remember living like that for a few years after my wife and I got married - being way too young and stupid. Most of it was my fault, suffering from bipolar disorder but too arrogant and too much in denial to seek proper treatment. I had to quit school, partially because I was about to flunk out anyway due to attendance problems - the work was never an issue, academia was always elementary for me - and partially because we were about to be homeless and it was important to both of us for my wife to finish her degree. Our housing situation was rough because there was a waiting list for married housing at her school and the married housing in which we were living at my school was very limited - much more so after our neighbor did something stupid and burnt half the place down. Fortunately, we didn't lose anything but the roof over our heads. We could have been going into enormous debt by living off of student loans but, even then, that was a trap we knew better than to fall into and sacrifice even more of our future.
For some reason, we were also hesitant to pursue government assistance - excepting utilizing the free clinic for illness and birth control - for some odd reason, probably somewhat irrationally thinking that it was really for people worse off than we. We were also, due mostly to my arrogance, reluctant to accept help from my parents who, to be honest, have never been in a financial situation to where they could really afford to support anyone but themselves. Even so, they've always been good with money and lived comfortably. If they could do it, then we could do it.
Our next apartment was a veritable crap-hole and we were only able to live there for a few months. Apparently our neighbors there were running some sort of prostitution / drug den out of their apartment and the building owners were looking the other way for a cut of the profits. As a result, the police eventually stepped in, arrested everyone, and we were left again without a place to stay.
I had been pretty lucky in high school and early on in college with good, relatively well-paying jobs - able to work and get experience in my chosen secular field of IT. Unfortunately, we had taken that for granted and spent our extra money on stuff rather than saving for the future. When my boss decided to close up shop, I suddenly found myself looking for employment in an overly saturated field - at least in this area - with seemingly no one hiring. As a result, I ended up working two or three part time jobs at a time - usually in some sort of crappy food service position - until I flaked out the next time I hit a bipolar-depression cycle.
Ironically enough, those good jobs I had early on then came back to bite me in the rear. I was trying to get anything as close to a good job as I could in any field, including trying to get a shift manager position at both McDonald's and Burger King. Both places turned me down for the same reason: the managers looked at my application, saw those previous jobs, and decided that I would get bored with that position and quit and/or jump at the first chance I had to get an IT job once the job market picked back up. As a result, I always seemed to be stuck getting the kind of jobs where they expect high turnover and don't care too much how long you'll stay. Crappy, low-paying job after crappy, low-paying job.
The car maintenance thing is a real issue, too. Keep putting in the cheapest oil you can find and stretching the time between oil changes for too long and you end up with a blown main seal and a seized engine.
Meanwhile, my wife was able to finish her degree plus the necessary amount of graduate work to sit for and get her CPA license. Unfortunately, the best thing she could find was a part-time job in her field. Now that school was finished, though, she was able to take on that job and still work a few hours as a cashier, so our money issues were starting to look up, just a bit.
Eventually, her hard work was rewarded with a full-time position and, after almost five years of marriage, we finally had health insurance. About a year later, I got a lucky break and was able to get a position in my field, as well. We were able to turn the corner and get what was, for us, a good apartment.
We've never looked back. Today, money isn't an issue for us and we're able to regularly help others each month avoid many of the issues we faced. It's very rewarding to have someone come to you with a car problem that's going to leave them without transportation for a couple weeks - or until they can manage to scrape together enough money to pay for the repairs - asking if you know of someone who could lend them a car for a few weeks so they don't lose their job and be able to simply give them the money to fix their car and provide them with a rental while it's being repaired.
Of course, another big part of the problem - in our society as a whole - is that it's often far more expensive to work your way out of poverty, especially if you have kids, than it is to stay there. There's a fairly large no-man's-land in terms of household income where assistance stops but you've still got a ways to go before you can really provide for the household.
Travelling to work costs money; car payment, car insurance, car maintenance, and gas add up to quite a bit out of each paycheck when you're working from one to the next. Heck, even working costs money; clothing, extra food costs, and daycare take chunks out of those paychecks, as well. Add in the fact that, all of sudden, you start owing taxes because you're now making too much to qualify for all of those tax cuts and that last raise somehow left you with less money out of each paycheck.
It's much easier to work just a few hours a week at the closest fast-food joint, sit at home on your butt most of the time, collect government assistance, and not have to spend all that money on transportation costs, work clothes, and daycare.
Our welfare programs seem to reward those who choose to remain in poverty and make it more difficult for those who try to work their way out of it.