I've got a 97 2.5l/auto that I have mod'd and wheel. I've had it for 6 yrs now. It was not optioned at all other than radio.
For my high schooler(s) coming of driving age, I picked up a cheap another 97 TJ this past summer. This one is a little better optioned with 6cyl/auto, ac, stereo, hard doors, and other newer items on it.
Biggest thing you will face with a high schooler is the peir pressure to do something stupid since its a Jeep. It will be small compared to other potential economy-style cars available. Being a convertible, things will be stolen and top/door damaged to get to them. Being a kid, music is usually played loud and with the convertible, everyone will hear it, even the theives. Jeeps are easily stolen as well, so if you do purchase, take the necessary precautions.
However, if your kid is responsible enough, understand the troubles it could bring, has a good head to make proper decisions, then I don't see a problem. The 4cyl will do good as he'll be hard to get speeding tickets. Do make sure he understands it will also not corner like his friend's Honda. The 5-sp (AX-5) are prone to loose their synchros above 120k. The D35 rear axle is good for basic street and trail use. There is a large following for them, replacement parts and upgrades are readily available, they are easy to work on for yourself/beginners, they are utility style so getting wet inside won't completely destroy it. Clubs are also a good way to get involved with wheeling as well as understand the Jeep and its capabilities.