[Perfectlap]

well if you are concerned with people who know nothing about Porsches have to say then by all means go for the 996 and don't look at the Boxster at all.

Since 1997 I don't think I have ever read anything but stellar reviews for the Boxster in every well regarded sportscar magazine. (you know the guys who actually drive these things). Top gear even named it the best sportscar in the world. The Boxster is the first and only full blooded convertible Porsche has built.
When the Carrera GT was designed they put the engine in the middle (just like Boxster and NOT the rear like the 996). Tells you something about what they think the best layout is for a HIGH performance car.

The Boxster and the Carrera are two totally different sportscar concepts.

asking should I pick a Boxster or a Carrera is like saying should I buy an M3 or an X5. Roadsters are Roadsters and Coupe are Coupes. If you want the 'flash' of Porsche and top down fun consider a 996 Cabriolet. But that's a compromised sportscar in my book. In Europe they really look down hacking the roof of a serious Coupe.

If you want a convertible go with a Boxster, there isn't a better roadster availble for less than $100K. Make sure you get a BoxsterS if you spring for it. In used values its not worth passing up.

If you want sports coupe there are way better options than a 996 for the money.
A beautiful car but very over priced for the performance on paper. But since your dealing with used its a decent option for the money. I plan to add a CarreraS to my stable as my "practical" car in a couple of years. I think the prices are still not quiet at the sweet spot of residual value. But as far your 996 I think you find a lower mileage model if you keep looking.