My '89 S2 has been my only daily driver for over 5 years, done 30K with it. Great fun! It's roomy enough for 1 or 2 people with a surprisingly big trunk, it's easy enough to drive around town and doesn't drink you into bankruptcy.
My cam chain broke at 130K, one of the biggest rookie mistakes. No bent valves though, but still expensive. Everybody will tell you that cam belt, chain, tensioners and rollers HAVE to be documented or recently changed, and there's a reason for that! My waterpump (original '89!) broke last year at 155K and I replaced it myself, along with the cam belt job. It's not rocket science, you can get good instructions with pictures from almost any decent 944 enthusiast site.
I saved almost $1K over factory prices by comparing prices, doing some research and buying leftover parts from club members. For example a waterpump for 16V engine is over a grand at Porsche, but you can have an aftermarket LASO pump for around $200 (I'm talkin European prices here). I payed $35 for a used one with 10K on it. Works for me!
I ripped out the back seat, put on a stiffer and lower suspension, there's a foot of snow outside and I'm still driving it and loving (almost) every minute of it!