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I had a 944 for a few years and put quite a few miles on it, great highway car, I agree, better than an early 911 in many ways.
As a matter of fact it was better in almost every measurable way than my SWB 911's, A/C, heater, it was a real car, pretty much a normal car like so many other cars out there with a water cooled engine in the front. And that is the rub and why I do not think it will every become something special, because it is not really that different from other cars.
A 944 is a good car, but so are a lot of other cars. What sets it apart other than the badge? nothing really. Nothing really unique, like engine location, for instance.
Audi UR Quattros are way more important and unique than a Porsche 944, and the UR Quattro is barely getting some love now. Maybe the 944 will go up, but I would not look for anything stratospheric.
As for what people on the street think? In my experience they think an old SWB 911S is a poor man's Porsche and a 944 is showing money, I think because it looks newer than a 911.
The only car I liked driving almost as much as a SWB 911 is a Alfa Alffetta.
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