[Perfectlap]

I think you have buyer's remorse about buying a grand touring, not so much regret in buying a Carrera. Had you switched to a 964 or 911 from the air-cooled era you'd be happy. Maybe a Targa to compensate for the lack of a drop top.

The 993 layed the ground work for the 996 as a more insulated and "modern" coupe experience. The 996 layed the ground work with a longer, wider Carrera. The 997 went further and now the 991 is a 'flattened' version of the 997 grand touring car. All previous Carreras had better feedback and were size approriate.

If you wanted to keep it water-cooled but wanted a coupe experience the 987.2 Cayman S would have kept you happy as well.

When I was first shopping for the Boxster I was actually shopping for a 996S. I also drove a C4S. And then a C2. All felt way too big, way too plush, and the understeer in the C4S was an absolute no go me. Then I got in the 986S and it was game over. This had everything I wanted as a roadster fan and I kept about $10-$15k in my pocket? What's there to talk about? To seal the deal it was in the exact color combination and it had under 9K miles.
In retrospect I should have bought a 964 RS back then and picked up a second car for winter like a Wrangler or something. Then once the market crashed in 2009 I would have picked up a pre- PASM 986S on the cheap. Although with an air-cooled Porsche, imho you'll always need a water-cooled version as well.

P.S.
Regarding the 996/997/991. These are workhorse Carreras. Sure it would have been great if Porsche kept them at Cayman proportions and kept the high fenders of the air-cooled cars but these are 911's that you can actually drive all year without worrying about depreciation. If you put one in the wall at your local track, you'll probably live. And once you've walked away you can go out buy another within a day at a bargain price relative to performance and experience. The fact that a weekend warrior could get within a couple of seconds of Porsche factory driver says a lot about what a huge step forward in performance, certainly on a cost basis, the 996 was. The 991 pricing is now officially absurd but I think years from now the 996 will mark the begining of the era of 'fast and practical' when it comes to the Carrera. And no "leak of the day" mystery on your driveway floor or costly engine rebuilds as regular part of long-term ownership. There will be Carreras you can drive, a lot, and Carreras that sit in your garage as an antique.