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I haven't driven an NSX, but I did own a 987.2 Cayman S and loved it. They are quick cars, especially with the PDK gearbox, headers, and a tune. The NA flat 6 screams at high rpm, and the whole experience is like driving a Ferrari 458 that's been turned down by 30%. Few cars can satisfy in the same way. I only sold mine because I was leaving the country and couldn't take it with me.
There are three types of Cayman owners -
1. Those that admittedly couldn't afford a 911
2. Those that couldn't afford a 911 but pretend like they believe the Cayman is a superior car... and get ultra defensive about it
3. Those that truly get it, and understand why the Cayman is so special
IMHO, the Cayman is the perfect car for enthusiasts that fall into category #3. I daily drove mine 3 hours per day, including stretches of back roads in the desert with no real traffic laws. The Cayman would have been equally happy on a race track with minimal additional prep (though mods do improve it further). The two trunks were awesome, and maintenance was very reasonable.
Caymans will continue to depreciate because they are the entry Porsche. People buy them and can't afford to maintain them, unlike the customers with the means to purchase a 911. Enthusiasts see them as second to the 911 ("if the 911 is also a Porsche sports car, why buy the Cayman unless you can't afford the 911?"). The general public can't tell the difference and only see a Porsche.
The #1 rule of collectability is people want what they can't have. If Porsche continues to downsize and go turbo-only, the Cayman may appreciate in 20 years as clean examples get harder to find. I don't see them doing anything crazy like the air-cooled cars, but they will probably fare better than the 944's being mid-engined with a flat 6. Expect to lose $10k-15k over 4-5 years and 20k miles.
If you were looking for an all-around single car, I'd say go for the Cayman and never look back. But as a second or third car, the choice gets more difficult.
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