I recently bought my 01 S after a long search for a 00 -02 S. I preferred the simple lines of 00-02 although my second choice would have been a special edition 04 if available.
I was lucky enough to find one with the options I really wanted ... PMS, Sport Package & the rare Sport Design Wheels!
I could have easily afforded the 987 (05-09) but they were not even on my radar as there is something satisfying in owning the Mk1 of the S! I drove the new Boxster S just recently ... amazing! But I still like the 986!!
Would you buy newer if you could?
Porsche Boxster S - meet the ancestors - Autocar.co.uk - YouTube