Having been to the Cayman Tech session which PCA / Cayman Registry / Porsche of Arlington put on yesterday in Virginia, a couple things came up:

(1) Have an inspection done on all potential leaks, including anything from the back of the engine (Rear Main Seal is a potential failure area with Gen 1 engines - the head mechanic indicated a key cause is starting the car from cold and regularly revving to the redline, like one might do at the track, which causes three different metals in the engine to expand at different rates). RMS damage, while it is stressed by the dealer to be extremely rare, is expensive enough to repair that Porsche will issue a new engine rather than have the dealer take apart and repair the old one. If the car was a track toy, there is naturally a greater risk than if it was a daily driver or a garage queen.

(2) Check the rubber O-rings and piping for the air conditioning system. If the air is not turned on regularly (even during winter), the piping may go through expansion/contraction, and the rubber O-ring (gasket-like fittings) and tubes could crack and freon leaks out. My O-rings at the firewall were replaced 7 months after buying the car (under warranty), but as the air conditioning compressor is in back, the condensor is in front, etc, there's a lot of tubing under the car, cleverly hidden by those innocuous-looking black-plastic panels that give the bottom of the car a flat, dull (but undoubtedly aerodynamic) look that harkens back to the 356. The brake fluid lines and power steering lines hide under those panels as well, with the power steering coolant lines making nifty curly-cues under the driver's seat to cool the liquid in the pipes. Needless to say, look for leaks where you think none might occur given everything is supposedly in back of the car.....

Happy hunting!

My thoughts are these....I had a 2007 CS, 18" wheels with stock suspension, it was red with tan interior...I ended up trading that for a 2009 base Cayman with what for me were nice options: the prime reasons for the change...given that I use it daily and don't track it

std suspension seemed hard for driving around town...on less than perfect roads...getting the adjustible/hyrdo suspension would cure that; I never really got over how "cheapie" the interior felt; and for business there was no simple, clean way to install BT/ipod...so it integrated nicely with hands off use; I also am very leary of keeping a GEN 1 car for long time....due to RMS and intermediate shaft concerns, while some don't worry nearly every 2005-07 Porsche I looked at...the sales guy proudly noted that the RMS was fixed...also if you were to get a GEN 1 I would strongly advocate geting one with the Porsche extended factory warranty...I certainly got my money's worth...clutch cable, thrust bearing, new key setup
the GEN/2 base model is nearly as fast as the GEN/1 CS model...neither model has alot of torque below 4000rpm...and I am not into traffic light racing or tracking...GEN/2 has new block which hopefully cures some lingering issues with the prior engine, it seems to ride much better, the car seems to have a nicer grade of interior materials and better overall fit and finish...the GEN/2 is faster...and with the hydro suspension should ride much better....though I am a little leary of the new DFI systems which seem to have some issues...as VW and Audi have had

Another thought I would offer is about garage queens...while body and paint wise they should be perfect...I have always had a better experience with cars that are driven on a regular basis...and if you get a GEN/1 I would suggested getting one with the extended PNA warranty....they go through the cars when they certifiy them and personally I am not enthused about paying for repairs on these cars....just my thoughts...