I have a 2000 S bought in June 2014 with 10,800 miles (!) Arctic Silver, black leather interior. I put 4000 miles on it from June to early November.
I never drove a base but I am very pleased with the performance of the S and think I would find the base underwhelming if I compared the two models.
Love the windstop
Don't mind the plastic window
Don't have heated seats and, since I store the car in winter don't miss them
Very much miss cruise control, I've do a lot of freeway miles and would drive the boxster more if I had that option.
Don't have any cosmetic or audio upgrades and don't miss them, rarely listen to the stereo except on long, dull rides and I don't have cruise control so I take the car with cruise and a good stereo then.
Larry
The Bald Eagle