its one of those situations where, you feel bad, it obviously is a crappy month but, can't keep mouth(keyboard) shut. You took out a loan for what sounds like the majority, if not all of the car and weren't responsible enough to drive safely. I might be wrong but it sounds like, renting a place with someone else, sounds like you're young, wtf are you doing spunking 22k on a car when you "could" just get around in a 1-2k thing, without getting into debt, without paying interest(you'd imagine the 18k will be 25k at least before its paid off).
But you can take some positives, your friend who you lived with, its freaking nuts, its not a terrible thing you have to move out so put that in the good things this month. You can't feel guilty, you tried to be nice to the guy and he craps on it, his choice not yours. So you can leave, know you did what you could and be happy not to be living with a psycho.
The girl, well, she'll have to come back at some point to pack up, offer to help, might get a shag out of it, she can still be a friend and she might not live there for long. Even with family its hard to immigrate and work in the US so theres every chance it would be short term.
Overall learn lessons, a house is really the only thing to go into big debt over, ever, anything else is really not a good idea until you're financially secure.
Also its worth looking into the insurance, possibly ask a lawyer, the dates thing really shouldn't matter, yes its a technicality, maybe an important one but an honest mistake and probably something that some group, WHICH or something would maybe like to fight over. Its worth looking into, and having someone else verify they tyre's were really not legal, maybe they were and the insurance were being overly quick to judge as a way to get out of paying. Insurance companies will always look to screw you out of paying up, just because they say no at first doesn't mean a fight can't change that to a yes. for 22k, its more than worth talking to some people to see if anything can be done.
The Job, unless you loved it, see it as an excuse to go get the job you really want.