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It's all about supply and demand, really. The air cooled cars are classics now and were never built in the numbers that todays Porsches are. Factor in the number of cars that have been destroyed over the years, some way or another, and you're looking at a pretty small number of cars available. At the same time, these cars are still desirable for those of us who lusted after them as kids and young adults, and we have shown a willingness to pay good money for them. So the supply is fairly low and the demand is still pretty high, which is what keeps the values up on these cars.
The 996, on the other hand, as good as it is, is a victim of it's own success. It sold in such numbers that even though most of them are still in pretty good shape, there are so many of them available to the second hand market that the values are being driven downward. This does not diminish the quality of the car one bit, however. It simply makes the car more readily available to those of us who are willing to spend new car money on a quality used car.
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