I've owned some air-cooled 911's, and currently own a '98 Boxster. I can attest to the fact that it's a fun car to drive, very well balanced, and certainly "quick" enough to put a smile on your face. Mine is the ultimate hair-dresser's car, as it's Ocean Jade Metallic, but I've had other Porsche owners track me down just to see it close-up, as it's pretty uncommon. My wife was actually pulled over by a police officer so he could give it a closer look (not sure if it was my wife, the car, or both)!
I did look at an '03 Carrera that a friend recommended, as it was a rare color, original owner, and low miles. I don't recall the exact color (some hue of blue), but it's definitely a different car. Noticeably quicker than my Boxster by a wide margin, but I don't know that it was as fun to drive overall. I guess the underlying theme is that I still have the Boxster.
Now, given the opportunity to buy a 996 Turbo, I might be in a tough situation!