[I don't quite get your logic. Why pay more for a coupe (Cayman S) when you can have the roadster that you really want (07 Boxster S) with the same power (295HP) for less?
As I tried to explain below to another poster, it's because I would rather have 1 car than two at this point, and the Cayman seems like a better bet than the Box, if that's the case. But if my love for the Roadster prevails over my desire to have just 1 car, then I'll go for the Boxster and keep my GTI as a 'practical' car. Keeping and (paying for) 2 cars is $$, so the TTR will go and I can manage a non-S, and my GTI. Is that clearer? 
Frankly, I am surprised by how many list the xenons as a must. Just don't get the hype and they were at the bottom of my list.
I guess it's because the HIDs on my GTI and TT are alot better than any of the non-HID lamps I've experienced on other cars; sound as if that may not be so much the case on the Porsches...
Dollar for dollar there is nothing on the options list of a Base Boxster that can beat the 3.4L engine upgrade (i.e. the "S upgrade") -- both in performance, everyday feel, and resale value. Of course, IMHO and to each their own.[/QUOTE]
Can't argue with that at all, although on fairly short test drives last year, I didn't feel the 3.2 was dramatically better than the 2.7l. I thought both had great response, quite flat torque curves, and rev-ability, though neither amazed me with the amount of torque - I'm comparing to two chipped, turbo cars. The 2.7 is way off what the GTI or TT put out in terms of torque. Yet, because of the things I just listed, as well as curb weight, it never felt under-powered. I will be driving the variocam-plus 2.7l this weekend, albeit in a Cayman.
Money and the practicality (almost one and the same) issues hold me back from the S. To put it another way, the only 'S' I can afford is the Cayman, to my way of thinking, as odd as it sounds. Initially more expensive, but I would be unloading 2 vehicles instead of 1, not to mention insuring, storing, maintaining and generally squandering my time obsessively, over 1 instead of 2 cars! Better in the long run, I think. Now if you guys convince me the Boxster S is every bit as practical and good a long-term prospect as the Cayman S, then it's a win-win! BTW, I've never been this undecided about a car before; I never had to shop or compare, because there was only 1 vehicle I really wanted. But these 4 Cayman and Boxster models are giving me fits!