TL;DR I'm feeling completely defeated. I don't know how much further I am willing to pursue my education before it's more sensible to cut my losses, drop my old dreams, and go do something else with the other 2/3s of the life I ideally have left.
I had to put school on hold about a year ago, because the Financial Aid I was receiving wasn't covering my living expenses, and I was making payments on a car to replace the old one which was destroyed in an accident a few months before that. I had a messy withdrawal, and by the end of the semester some of these ended up as E's instead of Withdrawals. Despite meeting with the Ombudsman, Financial Aid, Registration, Student Advising, and so on, they apparently couldn't retroactively withdraw courses unless I had been hospitalized for a physical or mental reason that semester. As a result, I wound up on Academic Probation.
It's a Catch-22... I need Financial Aid in order to be able to afford to register for classes, but I need to register to retake all the courses I didn't properly withdraw from before I can get off of Academic Probation and start receiving Financial Aid again. As a result, I took a 2 semester work-hiatus, saving up by working multiple jobs, to pay for the classes out of pocket.
This afternoon, just as I was getting ready to sign up for the Winter Semester, I find a hold preventing me from signing up for classes. 6k of last semester's Financial Aid was uncredited after it had been used to pay the tuition for all the courses I got E's instead of Withdrawals for. This turned into 6k of debt, which I wasn't informed of until I tried to register. Since it had been unpaid, this debt has since been sold to a collections agency. I've got to take it up with them before I can register now.
It's like every time I seem to have taken care of the problems I face, just as my head pokes out of the hole I was stuck in after months and months of climbing, I discover that that hole just lay in the bottom of an even bigger hole all along. Though likely just depression, pushing myself forward has always been hard; on the positive side, that effort has made me more adept at emotionally dealing with disappointment. Still, there is a limit to my strength of will and tenacity. I'm getting dangerously close to it.
I want to blame the fiscal and familial situation I was born to, and a good part of it was due to mistakes and personal weakness... but I don't think that, at this rate, I will ever be able to earn the degrees I want to. I can't see a way forward, but if I give this up I'm going to need to reassess a lot about my life, and where I'm going. I really don't know what to do, and I feel like I've been generally defeated by life.