READ MY THREAD ABOUT MY 97 MAINTENANCE COSTS!
http://986forum.com/forums/performance-technical-chat/35985-maintenance-over-past-year-ooch.html
If I had to buy another one I would go for a newer one just so I could get a nicer interior. Sure its the same design but the latter models seem to be a lot nicer.
Given both of those things I would choose a 97 thats been very well maintained then a 2000(given the 2000 cost penalty)