Which one for my next car, 996 C4S or 2007 Cayman ?

I work remote so don't really DD. My previous DD was my 2007 BMW 335. I had that car since new but sold it last month. My second car is a 2003 996 TT which I purchased last Oct. love the car and is really a weekend driver; 38.5k miles on it now. I miss my 335 already and thinking I need to buy another car. The ones I've been looking at are 2007-2009 Cayman S, 2003-2005 996 C4S, 2003-2006 XKR (14-21k $$) and 2004-2006 SLs (600 or AMG). I missed out on a 2006 XKR Victory Edition that sold for 19k and now looking at a 1 owner C4S (needs major service) or a 2 owner 07 Cayman S that will also need a major service soon too. Mileage about the same ~60k and price as well. I've been looking at Caymans for a long time now and think I need one but I just love the way the C4S looks plus this one is a 1 owner car.

As you already have the ultimate 996 with the Turbo, I'd opt for the Cayman, especially if you're going for the "S" model. You'll get a much better interior, and a much different experience than owning two 996's, especially the C4S, which is basically a neutered Turbo. I wouldn't even think twice about it.

As a 981 Cayman and previously 987.2 owner, I'd say go for a Cayman especially since you already have a 996 turbo. I've been liking the 996 C4S a lot lately and hope I can add one to the stable at some point in the future but agreed with what Jon said, think you'd appreciate something a little more different such as the mid-engine Cayman platform.

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Easy choice. Cayman! When you feel like you need a change! You can alway jump into the TT go a tad bit slower and pretend it's a 4S!

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I'd do the Cayman in a heartbeat, nice choice to have!

996TT AND a Cayman S!!! Lucky Dawg!

Another vote for mid-engine. You already have an awesome tail-dragger...give the mid-engine cars a try. Although you may find yourself neglecting the Turbo more often...

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I also have a 981 Cayman S. And it's a great 1, 2 punch - a really fun stable!!

Cayman. For the reasons others have stated. The 987.1 model was made from '06-'08, and the 987.2 from '09 to '12. If you can swing it (and if you can find them), the 987.2 has a better engine (no IMSB), direct injection in the 3.4L (S engine), and availability of PDK. You will find a definite price difference between the first and 2nd gen cars, and there were significantly fewer gen 2 cars produced.

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Glad to hear that you enjoy both, I really like my 981 but have been wanting to go for an older gen car now as I think you do give up some character and driving feel on the newer ones but it's a tradeoff for modern looks, interior and features, warranty, etc. Love your combo, especially that you have one PDK and one six speed, if I could do it again I'd go for PDK on the 981 and 6 speed on the older gen. Get the best of both worlds that way imo, sometimes I want to be lazy and just cruise around in Auto, and the PDK is fun in it's own way for spirited drives as well, love the more pronounced change in exhaust note octaves as you quickly upshift through the gears and the nuances it has depending on how you interact with the throttle pedal.

My only vote AGAINST the Cayman: You'll get a little sloppier. The mid-engines are so hard to upset unless you're pushing it that you really don't have to be as attentive as with a 911, even with the "tame" 996. When I moved from the Boxster to the 911, I was surprised at how many corners I was taking not-quite-right and the Boxster was making up the difference. Same corners, same speed in the 996, and more attention is required to keep PSM from telling me I'm being lousy.

Thanks for the feedback guys. Have to say I am surprised by the number of Cayman responses but it does make sense since I already own a TT. I will say I am leaning towards this 996 C4S since the one I am looking at is a 1 owner car, has more space than a Cayman, Looks like the TT but is different at the same time, and would be a safe car to drive in the winter while the TT is garaged.

I love the style of the cayman but at 6'4 230lb's I don't imagine I would fit so well. Plus the times when a couple friends wont to go for a rip, throw one in the back and your set, girl friends of coarse

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That's a good point (about interior room). I'm 6'-4" and 215 and I just fit in my 987 Cayman. Legroom is what's in short supply. The 981 does have more room however and it feels much more like my 996 felt. 981 has more legroom and more width, and similar or better headroom too.