In considering the usual "Should I get a Boxster or a Cayman?," question, there are very few issues to consider. The Cayman always is given a few extra horsepower. The extra rigidity of the Cayman is something you're unlikely to test off the track, simply because even the Boxster handles like a champ. The Boxster is unquestionably a slightly better deal. (Whoever heard of paying less for a convertible?) Either car is enormously fun to drive, and the real decision should be made on the basis of one thing--do you want a convertible?
In considering the usual question, "Should I get a Cayman S or a 911?'" the main reasons for choosing a Cayman are it has the motor in the right place, it's arguably even more beautiful, it brings all the same excitement, and it cost way less. There is only one reason for choosing a 911 over a Cayman S: snoot factor. But you'll pay heavily for showing off and have nothing else to show for the huge expenditure. The Cayman S is now the virtual equivalent of the 911 in all but price. Read the magazine comparisons.
Absolutely beautiful! Hong Kong native Pinky Lai's redo of American Grant Larson's boxster even outdoes the original.
Reliability & durability
Historically, sports cars were amongst the most unreliable of all vehicles. While early Caymans would occassionally suffer catastrophic engine problems, it was otherwise remarkably dependable. Since the problem was fixed in model year 2009, the car has been relatively rock solid.
I have the so-called "base" model--a designation Porsche gives to embarrass the buyer into spending another $10K on the "S" model. The 5.4 seconds it takes my slower "base" model to reach 60 probably beats 99% of the cars on the road for acceleration. Please try it before assuming you must have what the marketing people want you to think you must have.
As for the 7-speed PDK transmission, I--an eternal hater of automatics--have finally waved the white flag. It anticipates my gear changes before I do so consistently that I've simply given up shifting. Moreover, with 7 speeds, when you DO shift to manual (always an option with the PDK), you find yourself shifting constantly to the point of annoyance.
Safety & braking
Great brakes. Spend the extra $8,000+ (I ain't makin' that up!) on ceramic brakes ONLY if you will race the car. Otherwise it's completely nuts to buy that option.
Interior storage compartments
Remarkably clever and useable storage--both front and rear trunks, but also the many little closeable cabinets.
Price or payments
Predatory cost of an endless list of options. Think before seriously considering any of these. The base seats are already mostly power. Can you really not pull the spring-loaded seat forward a few inches? If you don't get the "multi-function steering wheel" will it really kill you to reach 3 inches to turn up the volume on the radio? Is there anything more unnecessary or useless (or even aesthetically questionable) that paying way more for even taller wheels? (The base model comes stock with 17"wheels and the "S" comes with 18" wheels. Bigger starts to make the car look like it's owned by a drug dealer.) That said, the overpriced 7-speed PDK is such a pleasure that I suggest bending over and paying the $3200 to add it. Amazinginly it improves accelleration and gas mileage, both of which should tell you this is no ordinary automatic.
Also, parts and service are way overpriced. But what can ya do? It ain't a Kia.
All you get is white, yellow, red, or black. Porsche (like BMW) hits you for anything else.
If you can't buy this car without a loan, consider a Miata instead. No one NEEDS this much car. You'll have much of the fun with the Miata and not put yourself in financial jeopardy.
Otherwise, it's hard to imagine that you could have more fun with a car that's reliable and works as a daily driver. Sure, Ferraris are sexier and Lotuses are more hardcore, but you can't drive either one on a daily basis nor could you take a trip on one. This car is as close to combining Toyota reliability with Ferrari excitement as you'll ever get. Yes, it's overpriced, but there's more than a shred of truth to the Porsche marketing hype--"Nothing else even comes close."