You can do it brother. Stick with teaching and in 35 years when you're ready to retire (and you won't even be 60 yet unless you started college late), you'll have a decent retirement and nothing to worry about.
1) Stay with that low rent for now until you get your other debt gone.
2) Normally I would say if the student loans are at 5% or less, then take the life of the loan to pay it off, but in today's world where things are less secure than they were a couple years ago, I would probably take the life of the loan to pay them off even if the rate is higher; they'll be gone in 10 years. I hate that, but it's prudent right now. Will be nice to not have that to pay each month though, so if you're feeling pretty secure in your teaching job, go ahead and chunk them down.
3) Medical bills -- you didn't say how much they were, but just get them gone within a year if you can.
4) Car -- I disagree that you need a NEW car. Maybe new for you. There are deals out there yes, but consider everything when getting a car -- rate of interest to pay (new is USUALLY better than used there), cost of insurance (used is USUALLY better there), total cost of the car, etc. Hyundai was having a deal where you could return the car if you lost a job within the first year (or something like that). Hyundai makes decent low-priced cars. Hard to go wrong with certain model year Hondas or Toyotas too though.
5) If you and your girlfriend do get married, THAT'S the time before kids come along to wipe out all debt and invest heavily in retirement accounts (403b, Roth IRA, etc.).
You won't be buying a yacht on a beginning teacher's salary, but you can end up making some decent money at the end of your career as a teacher, and then your pension in most cases is based on your salary toward the end of your career.
Do it brother! Teaching is very rewarding. Have fun.