The 987.1 (pre-'08) Cayman S that you'll find for under 30k is plagued by the IMS bearing issue that ruined 996 prices and early Boxsters, though. I'd spend ~40k and get a 987.2 instead. It'll hold value enough to make the price difference worth it, and even if a low percentage of engines actually fail, the peace of mind is very nice to have.

Plus they fixed a lot of other issues (better air-oil separator, more oil pumps, power steering heat soak) that will crop up if you ever take one to the track.

Overall I agree, though, it's a shame they keep holding back on the Cayman to keep the 911 on top. The 911 is an amazing car but there's no reason they should need to keep hacking around physics to keep the rear engine dream alive.