Let's be honest. There's really only one reason you want to buy your kid a car: to get him out of your dang house. Sure, at first it's just to send him to pick up his siblings from ballet and basketball, but then it's to get him to his after school job. And then to college, and then (fingers crossed!) on to a high-paying job that doesn't require that he moves back into his childhood bedroom -- the one you've already made into a sewing room. Whether you're buying new or recently used, remember that this may be the car that sees him through to adulthood. Buy a car that you expect will last that long, one that won't require too many repairs, and the next car he needs will be totally on him.