My background
Boxster -> C4 -> C4S (996) -> Cayman S
Reasonable amount of track time (~moderate driver)
Done 1,500km now, <3 months old.
I had sold my 996C4S and my friend lent me her Cayman S for a couple of weeks as she wasn't using it. I loved it. That's when my Cayman affair began. I had ordered a 997TT but was too disappointed when they didn't release PDK. I also felt the car was heavy and passionless when I dove it at Mt. Cotton and all of our group preferred either the Carrera S or the Cayman S over the TT (prior to driving the TT we were biased towards it). I believe manual and slush (auto) boxes are all but dead. What I'm in the queue for next is a GT3 RS - when it comes out with PDK (in 200X). I don't mind waiting. I'll keep that car in NZ, and the Cayman S in Sydney.

Things I love
Enough power: I don't know why there's some noise about a so-called lack of it - IMO it's perfect.
Mid engine - feels so good around corners, almost entices you to push it harder and harder (sounds good behind you). Very hard to make it go sideways.
Decals (pic below)
Ideal 'city' car that is good at everything, both on and off track
I did a motorkhana (autocross) in it a couple of weeks back and it was very impressive (PSM on and off). It beat almost everything there! (5/35) - and there were some nice things there!
The clutch - feels strong as, especially when upshifting with a few rev's on the dial and letting out it promptly - it does put you firmly in the back of the seat.

Things I wish I had
PASM
Sport button
Extra thick steering wheel leather
NZ style roads in Australia (windy, no cars, no police, safe)

Nice to haves
Bi-xenons (I don't drive much at night)
Rain-sensor (we have a drought so it's not too relevant)

Things that surprised me
Small carbon fiber interior package - previously I would say it was a waste of $, not now, it feels great. I would insist having it.

Things I still hate
Bose (enough said)

I don't miss my 4WD, except uphill in the rain. I do love the 2WD experience, feels great, and very interactive. It's a zippy car. It's not the ultimate P-car, but is such a ball to drive. I almost never used my Carrera back seats, and having two boots is super handy. I can see myself being very happy in this car until I replace it with a PDK version of the Cayman S!

Options
Sports Seats
Sport Shifter
RIMS PAINTED IN EXT
Instrument dials Guard red
C CONSOLE PAINT EXT
19" Carrera Sport Wheels
S/SEAT R/SIDE BACKRE
3-spoke st/wl smooth
Front spoiler lip paint
PARK ASSIST SYSTEM
Bose High End Sound
Interior carbon pack

I would love to find a few remote windy roads to drive it on, but the best place for that is on the track. I'll build the km's up and bring it there in a few weeks.