I had a 89 944T and it seemed to need repairs fairly often. I later had a '96 993 C4 and it had a few nitpicky things at first but for 2 years ran flawlessly. I bought it new. I then bought a '96 993 Twin turbo. It had 40K miles on it. It had some pretty significant things go out on it.
I've had my '98 Viper GTS for 12 years. It's required some work but not near as much as the Twin Turbo or the 944T.