Hey Chris, I recognize you over from S2ki.com. I enjoyed your post where you reviewed the test drives. I just picked up a Cayman S a few days ago and haven't had the chance to post it in car talk yet. I went from the S2000 to the M3 and now to the Cayman S.

In my opinion, unless you miss the top down aspect of the S2000, you will not regret getting rid of S2000 for the Cayman S. The handling is on par with the S2000 but the Cayman just feels more solid. It is more refined and has less wind noise while having a decent amount of storage space. The gearbox on the S2000 is better but then again, the S2000's gearbox is better than pretty much any other car. If you can swing it financially, the Cayman S is just a step up that you won't regret. Right now would be a good time to pick up an 06' for about 52k.