[Lukesportsman]

As soon as I saw the title, the 944 came to mind. Its modern enough to have safety in mind (compared to a less expensive 914) and comfortable enough that he won't grow tired of soon. He's young and the 944 will allow some room for modern mod's like his buddies Civics and the like. He gets A/C for his dates and a good alternator for his stereo amps. Cheaper to maintain than a 928, though an early 928 would get him in a slightly bigger/maybe safer car.

For a play car that wouldn't need to be driven in bad weather: 912 All the look of dad's without the running expenses that our boxster engines bring with them. Kind of like the ultimate VW in the eyes of highschool guys I would assume.

I would go for 944 first to make sure he drives safely before the 912 if my son was ready to drive. Luckily I have about 10 years. There are a few Boxsters at our local highschool, but maintenance cost are going to be higher.