If you are a waiter at a decent place you could pull 15k/yr if you are good in high school working a lot. I was a life guard whenever I wasn't in school or swimming and got $8/hr and it worked out to about 8k/yr. Waiters make a lot more than that around me normally, its a pretty stressful job comparatively though. On the other hand there is no way I could have saved 2/3 of that - my parents just kept forking over more crap for me to pay. Sucked at the time, but oh well.
Everyones' situation is different, if he has the money to spend, I'm jealous.
On the insurance note, my family always arranged it so our newest driver was on the cheapest car to insure. Maybe talk to him and see if he would be willing to switch primary cars with you insurance wise, and you could pay the more expensive of the two. Never know.