I would take the Z, my main reason would be that there are many 911's out there and the Cayman S will always be the low man on the ladder, that's what Porsche designed it to be. Putting that aside, if the car will be your daily driver get the Z, I would have a lot easier time sleeping putting a new Z through the daily driving rigors than a used Porsche. It wouldn't bother me as much to see a Z get the eventual wear and tear that a daily gets but it would bug the hell out of me on a Porsche.
The Porsche is the better quality car and the engine is in the middle making it the better handling car by far. Driving mid-engined, you realize quickly is the right move. The Z may have a bit more on the power side and the aftermarket is not as costly but if your decision is based purely on driving feel, Cayman S all day.
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2009 Carbon Fiber/Red 370z aka Trish: Sports Package, Meisterschaft full catback, Fast Intentions Longtube Headers, Injen Long Tube Intakes, UpRev Tune: Sold 
2008 Lotus Exige S Club Racer aka Bella, always leaves me smiling
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