I used to drive about 20-30 miles each way. I would spend $30 once or twice a week PLUS tolls. It's so much easier being ~5 miles from work.
My insurance isn't terrible. When I was added to my parents' plan in HS/college, it was high but not AWFUL, but I'd never gotten into any accidents. When I graduated, I broke off of their plan onto my own and it's not too bad for full coverage. It's not $750 though
I hope he gets a job soon so it can ease some of the pressure on you.