I've definitely had my share of poor experiences. I use to work for a famous gaming software company, but I worked CS, so I made really crappy money. Living paycheck to paycheck did not help my situation out at all, so I decided to move back in with my mother, so that I could transition.
Currently, I make roughly anywhere from about 220-330 dollars a week, so I fall below the poverty line for my state (Alaska). I looked into getting insurance through the university here, which amounted to about 120ish dollars a month, and even then they may or may not cover hormones, therapy, doctor's visits, ect... for transgender people. I went ahead and looked into my options on the healthcare market place to see what I could potentially qualify for and luckily I ended up with a pretty decent plan for like 40 dollars a month. As far as I can tell from their plan description, they don't exclude transgender services, but I have a feeling that something will come up along the way. I guess I will find out for sure when I head to the doctor's office in May and they decline to pay for the service.
More to the point, I definitely made sure to save up some money so I could afford to pay for it out of pocket. I set back my tax return and started to save my money from my job to afford HRT, the lab tests, and the doctor's visit. Luckily living with my mother allows me to set back as much money as possible to afford these particular services. She is totally cool with my transitioning, so that really helps out. As far as school goes, my transcripts are held by another school, so I owe them some money before they will release them. At the moment I decided to put off school, I need to transition more than anything at the moment. I'm already 27, for my own mental health, I can't put this off any longer.
As per usual, YMMV, my situation isn't exactly the same as yours, but I hope it helps out to some extent.