Insurance question. Has anyone else been in this situation? I can't be the only one.

So I'm a 25 yr old male. Been on my own insurance since 18 because my parents kicked me off of theirs on my 18th birthday. I currently work as a welder/fabricator full time and get my insurance through my job. I've been attending school at night part time the past year and a half, working my way towards being a respiratory therapist. Eventually, though, I'm going to need to quit my job to go to school full time and finish off my degree - and lose my insurance.. what do I do for insurance while attending school? There's no way I can just buy supplies outright, it would be insane - I had to do that for a little while after my 18th birthday and I'm still paying off the debts. Right now I'm on a Dexcom, and I know I'll have to drop that after I quit. But has anyone else been insurance-less for a couple years while perusing college? What did you do?

Advice is very much appreciated. I don't want to stay at a job that I hate just because I'm diabetic and need medication..