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I bought my 2008 Cayman brand new in April 2009 and sold it a few months ago after four years of ownership. After test-driving a new Cayman S with a sticker of $89K, I ordered a BMW 435i and have been driving that for about three months now. I am well aware that these cars are not (fully) comparable, but I'm going to offer some observations anyway.
Driving: My 08 Cayman had a stick, but the 2014 "S" and the 435i were/are automatic. The stick is more fun if you only have a weekend car for a toy. For everyday use, the automatic or PDK is superior. I spent a half hour today in a traffic jam and I would have about worn out the clutch and my left leg if I was in the Cayman. For acceleration, I hear that the BMW may not win according to the stopwatch but in the seat of my pants, it wins hands-down. Since I don't race anybody and don't routinely carry a stopwatch, the seat of my pants rules. The BMW engine always feels like there is a tiger in there, ready to leap, whereas the "S" starts out relatively slow but comes on fast. On a track, the "S" would be better but the feel of the BMW is intoxicating. I guess I just like the fact that the BMW power comes on at low rpms. For passing, the BMW has 8 gears and will readily downshift and it feels like flying. I supposed the "S" would do the same but didn't have the opportunity to test it. For handling, of course either Cayman will outhandle the BMW, but the only place it would make any actual difference would be on a track. The BMW already accelerates and corners so fast that it would be very easy to run into other (slow-moving) traffic ahead of me. I can still fly around turnpike ramps like in the Cayman; the BMW may actually be slower but without a stopwatch I can't tell. It feels very secure, which is all I care about. Just about any modern car has more performance than it can really use. I really wish we would go back to the days of MGs and Spitfires, those were a lot more fun than these racecars they build today. Heck, I'd buy a Miata if I could fit in it.
Style: Nobody can beat the style of the old Cayman. Prettiest car I ever owned. The new Cayman is still pretty but IMHO the changes they made did not improve the looks. It's okay but not excitingly so like the old model. The BMW isn't the beauty queen that the Cayman was, but it's still a pretty good looking car and has a strong street presence. With the 19" wheels and the M Sport suspension, it hunkers down and kind of resembles a Jaguar XK in a way. Even though it's merely an unobtrusive silver, it seems like it gets noticed at least as much as my old Cayman did -- but that may simply be due to the fact that it's a new model.
Practicality: I was fairly comfortable in either Cayman, but I have stretch-out room for my 6-4 frame in the BMW, can carry passengers in the back seat, and all my wife's shopping fits in the trunk. The BMW is a better highway cruiser, it's very quiet and the active cruise control is incredible. I'm getting between 22-27 mpg in it, which is comparable to my old (base) Cayman despite the fact the BMW is up 60 HP and at least 500 lbs. And I just love all the electronics. Everything is automatic. Very relaxing driving experience. Quiet. Peaceful. Not stressful. Yes, I like the electronic nannies. Blasphemy among some people. I know how to drive but the nannies help protect me from the idiots who don't know how to drive.
Value and Buying Experience: The Porsche salesman pointedly ignored my wife and insisted she wait in the showroom while I got to drive basically around the block. I knew more about the car than he did. I already had kind of a low opinion of the company and this did not help improve it. At the same time I could not simply forget my four years of Cayman ownership in which I had to deal with an incompetent dealer, an incompetent indie, and the Porsche company that never gave a SH!T about me ... until the new Cayman came out and so they suddenly discovered my mailing address to send me advertising, so the Cayman started out in a hole, so to speak. Both cars are nicely finished, but at $89K, the Cayman S had "almost" as many options as the BMW that I ordered with basically everything, and the BMW stickered at $25K less. BMW paid attention to my wife and seemed genuinely interested in getting and keeping my business. And BMW has called me several times and surveyed me about my car and my experience -- something that NEVER happened in four years of owning my Cayman.
SUMMARY: Car buying is entirely subjective. Almost any car can be used for almost any purpose. You guys that drive your cars on the track and are interested in that sort of thing, you need a Cayman. You guys that have the time and budget for a weekend toy car should get a Cayman. If you live in an area with lots of empty, twisting roads and have the time to enjoy them, by all means, get the Cayman. But if you have commuting to do or errands to run, and 99% of your driving is on city streets and freeways, the Cayman isn't bad but there are better choices. Basically if you are like me, the performance of the Cayman is basically wasted and yet you'll deal with the (relative) impracticality every day. For four years of Cayman ownership I felt constantly conflicted by this. If you are getting a practical car for daily use and just want a sporting feel to it, the BMW is a nice choice as would be an A5 or similar. I personally have more permagrin just from feeling the tiger lurking under the hood of the BMW than I ever got from my Cayman, but I know that other people have different experiences, and that's okay.
 

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SUMMARY: Car buying is entirely subjective. Almost any car can be used for almost any purpose. You guys that drive your cars on the track and are interested in that sort of thing, you need a Cayman. You guys that have the time and budget for a weekend toy car should get a Cayman. If you live in an area with lots of empty, twisting roads and have the time to enjoy them, by all means, get the Cayman. But if you have commuting to do or errands to run, and 99% of your driving is on city streets and freeways, the Cayman isn't bad but there are better choices. Basically if you are like me, the performance of the Cayman is basically wasted and yet you'll deal with the (relative) impracticality every day. For four years of Cayman ownership I felt constantly conflicted by this. If you are getting a practical car for daily use and just want a sporting feel to it, the BMW is a nice choice as would be an A5 or similar. I personally have more permagrin just from feeling the tiger lurking under the hood of the BMW than I ever got from my Cayman, but I know that other people have different experiences, and that's okay.

You have to drive whatever works for you,clearly for you the Cayman was a compromise, for me it is not. For me, my new 2014 Cayman S is a perfect and fun daily driver, bar none. Have owned 3 series BMW's before, and although they are nice cars,( my brother owns 2014 right now), they do not come close to the handling of the Cayman. Which happens to be better, by all accounts, than the 911. I happen to have known my Porsche Salesman for 15 years and he is the best !

Cheers
 
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