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I doubt anyone has ever regretted buying an S over the 2.7, but there are a lot of happy base model owners out there. Also, make sure you are comparing apples to apples.
For example, a 1999 base model had 200hp, the 2001 S had 250. Then the refreshed 03/04 models got an upgraded VarioCam VVT and the base model was up to 228hp.
Personally, I chose a 2003 base that was in excellent condition over a 2002 S that was a similar price but not nearly as nice. I wanted the newer facelift features, and it had enough low end power for me. (I was coming from an NB Miata, so I didn't need that much more!). Also, I preferred the gearing of the 5 speed in 2nd and 3rd gear -- I don't do a ton of highway cruising, where the 6sp is probably much better. It really depends on how you're going to use the car the majority of the time.
Drive as many Boxsters as you can before making a choice. I went with the base model, but again, I doubt you'll find too many people kicking themselves for buying an S (unless they overextended themselves on payments!).
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2003 986 2.7
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