Yo Ant,
Don't be scared. The Boxster is a great car. Yeah, the newer cars are better than the earlier ones, but they're all fine cars. The older ones just have a bit less power and a couple of...uh... glitches. I own an older one; a '97 in fact. For what I saved by buying an older model rather than a newer one, I'll risk having to fix it from time to time. Same looks, great fun, and ten grand less. So the newer S is faster and I gotta' keep a couple bucks in reserve for the inevitable repair. Whatever.
Some of us tend to forget that cars break. They all break. I don't care what you drive. If you want rock solid reliability, buy a Camry; maybe a nice beige one would be good. The money's comparable to a pre-owned Boxster and you can ride around in absolute anonymity, having exactly zero fun. Guess what? Sooner or later, it will break, and the Toyota dealer will knock your brains out for the repairs. That's just how it works.
This particular thread is about a '99. It needs a water pump, a serpentine belt a window switch and an alignment. Frustrating? Yeah maybe, but friggin' deal. The car is a '99. Look around. A lot of '99 cars are wheels up in the wrecking yard by now. Several of this particular car's "problems" are normal maintenance issues. Inconceivable that an eight year old car needs an alignment and a fanbelt? I think not.
Hey lejolierogue, I'm not picking on you, I swear. I'm just trying to make a point.
Just do your homework. By reading all the information you can find on this forum, you can become an expert in all things Boxster in a hurry. Be certain that you can afford to maintain such a car. They do break. Buy the latest model you can afford and be sure to have Porsche do a Pre-Purchase Inspection before you pull the trigger. Then drop the top and enjoy the crap out of it.
Also, buy the shop manuals and learn to fix it yourself. Most things you can do on your own, and there's a certain satisfaction in knowing you were able to beat the dealer out of his payday.