Back to the original poster's query- have been casually scoping/ researching 996's for possible 'upgrade' on a no hurry basis though i love my '87 coupe. Below are my objective findings by topic...

Speed: The July 1998 Pano story on the intro of 996 first got my attention. Although the author was struggling with his initial 996 impressions v.s the 993- he wrote: "Hurley Haywood has no such ambivalance... he unhesitatingly makes his argument: the 996 is simply, clearly, undeniably, and without any question the machine he wants for doing what he does: go fast. Very fast... Hurley offers another observation: this car makes the business of going faster easier." I will take Hurley's word for it.

Reliability: While there do not seem to be any hard statistics available- i believe in the axion "where there's smoke- there's fire." I have witnessed too many credible sources citing undeniable examples of RMS and catastrophic engine failure w/ 996. Probably fair to conclude 87-89 Carreras on average have a better history and reputation for reliability.

Safety: The (4) airbags in the 996 are becoming more of a factor as i transport my son amongst the hoard of SUV's. Also according to Hurley the 996 "... is more salvagable if it does get loose on a slippery track..."

Capital Deployment: In extrapolating trends of past decade, seems reasonable to conclude my Carrera will be worth close to its current value 3-5 years hence if i continue to carefully maintain it. However the prices of 996's continue their descent as i type this- no reason to conclude they have have hit bottom yet. The supply of 996 for sale v.s. the perceptions of reliability issues seem to have eroded prices- in addition to regular depreciation.

My conclusions: Here is the 'opinion' segment. Driving the 996 was an eye opener. It is faster, handles better, superior brakes, smoother, quieter, and less effort to drive. That said, there was an invisible 'layer' between me and the road that didn't exist in my 87. The noise, vibration (Bilsteins) and sensation of having your hands on the front wheels was completely absent in the 996- which is why i bot a Porsche in the 1st place. Less effort to drive is not a high priority.

Until and unless a really compelling deal on a 996 comes along, i will continue to transport son in wife's Benz and enjoy the 87. One thing i hope we can all agree on is that we like most flavours Porsche offers...life is short- find the one you like and enjoy it!

At one point, back in the 70s, several Ford models, including the Pintos, would explode if rear ended. Because of that, Ford was sued greatly by people who were injured, or by the interested parties of those killed. Since then, Ford has installed switches in their car that cut off the fuel when those cars are rear-ended. Anyway...
On the contrary, I want to hear about racing victories involving water-cooled 996s and 997s. That gives credence to the car which was enjoyed by its air-cooled ancestry. The problem is the GT3 is quite different, at least in the engine, from the standard water-cooled 3.4 or 3.6. The dry sump is one area, and I believe so is the bottom end I'm not certain, but I've heard somewhere that the bottom end of the GT3's engine is actually from the 993 engine. Someone correct me if I'm wrong.

turbo and gt3 bottoms are 964-derived