Hmmm. I owned a '66, '69 911T (modded to S specs) and a '74 S. All air-cooled of course.
I've driven quite a few newer 911 series, and though the performance is much better (and in some cases, insanely scary better), the early cars had character that most later ones lack, be it in sound (not just the engine, but overall sound) immediacy of the controls (you could feel the mechanical connection to the road through your butt and the steering wheel), and more. I've driven early air cooled ones lately and all that still rings true. The feel of the road, and what the tires are doing, through the steering wheel to your fingertips is just incredible. The cars feel much more like a thin mechanical extension of yourself. Absolutely love driving them fast on twisty backroads, but then again, after autocrossing them for many years, I can control them past the limits pretty easy, and know where those limits are so not to come close to them on the road).
New ones are faster, yes. They are more comfortable, yes. They are definitely safer and more "useful." Incredible cars in their own right. But... They are more isolated and don't feel as much like a second skin. The modern bulk is noticeable. The only exceptions are the GT2 and GT3 versions, and even then, the bulk and isolation is noticeable, even though you are not
as isolated from the world around you. In the quest for better daily driver qualities, they actually have lost something that made/make the early cars special. Gained a lot in performance, but for those of us who probably wouldn't track the cars, that doesn't matter quite as much (still wouldn't turn down a new one...
)