[Aerkuld]

I can relate to this in a way. My 944 never actually let me down and left me stranded but it seemed like there was always 'something' that I just needed to do. I would probably have kept it but my fiance (now wife) convinced me that a more reliable car was needed and talked me into getting the 996. The newer car is definitely a major benefit when it comes to social time rather than crawling around on the garage floor.
The only thing I can see with the Cayman is that you will be relying the dealer which may or may not be a positive to you. An older 996 might be worth looking at. It will be considerably cheaper initially and you can choose whether you take it to the dealer or do stuff yourself. Just a thought...