I have the Cayman I wanted. It's a base and not an S. There was a whole smorgasbord of Caymans for me to chose: new S's, pre-owned S's, demos, '07s, etc., but I selected the car that was perfect for my needs. There is no denying the power supremacy of the S, but the base car isn't a slouch. I don't plan to track my Cayman. Some this talk reminds me a bit of the guy who shows up on the first tee with a $500 driver ("because it hits the ball farther") but can't hit the fairway. I also see this all the time on my cycles. Guys who should be able to eat my Beemer's lunch can't get out of my way. Put some of the passion aside. This shouldn't be a passionate or economic decision, but a rational one. Buy the Cayman that meets your needs. If you find the base Cayman doesn't float your boat enough, then go get an S. One thing I'd do is be certain you can exploit the base Cayman to its potential before I'd blow wads of cash on soothing my ego or id.
I'm certain I've probably ruffled a few feathers, but the world is full of hot shots who struggle to (1) pay for their toys, and (2), can't use them to their potential.
And let's be honest, the teenager in the tricked out Civic isn't gonna care that you're driving an S or a base Cayman...neither is most anyone else.
