I sold my 1997 993 Carrera C2S after sorting all the little issues and regretted it. I had repainted/repaired the front bumper valiance, the door check, installed PSS10s and it drove like a dream. I sold it to buy a Boss Mustang Laguna Seca (so stupid).
Then I owned my '89 for 7 years, the longest I've ever owned a car, and enjoyed every second of it. Repaired items as-needed, made a few small upgrades (Bluetooth stereo, Monty muffler, better tires), and drove it everywhere.
I sold it because I poured a small fortune into a hot rod '67 Elan which I convinced myself was more fun. In many ways, it was, but the horrid Lotus quality wore on me and there was always a pervasive sense the car was going to strand me or kill me and I realized the tactile experience was grossly undermined by the anxiety the car created.
Finally, I picked up the '71 which in many ways is just right. It's so far from original that I can drive it guiltlessly and despite being 50 years old, it's reliable enough and I'm comfortable enough with these cars that I don't really worry about unexpected mechanical failures.
After bouncing around to a bunch of other marquees, I've come to the conclusion that there is a very specific formula to the air-cooled 911s that other manufacturers simply never replicated. You can drive them distances. They've got an intimate, connected feel that only a few vehicles can replicate, and most are far more expensive or far less reliable (or both). They're well built. They're reliable. Parts are readily available. They are also still very, very fun. Their values are more consistent than most of their competitors.
