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$7,200 off sounds like an extremely good deal if it is a brand new car (not demo). I would have thought 10-11% off (i.e. $5,500+/-) on a leftover brand new 2007 would be a very good deal. Be forwarned however, that the Cayman S is a real sports car and the TT is more of a sporty coupe. If you want the former, you will never consider a TT again after a test drive. I know Audi tried to go on a diet, but depending upon the configuration, the TT can still weigh as much as the Cayman S with an large Cape Buffalo sitting in the passenger seat. I think you beter make sure what kind of car you want before you cross shop these two. They are at different ends of the spectrum of two seaters.
Start there, but don't limit your search to your nearby dealers in New England. Everybody's inventory is accessible through Porsche's website. The dealer I bought from in Baltimore ships cars to California.
I would think a similarly equiped 911 coupe (base) would be about $18-20k more, in the $73-75k range after discounts (MSRP of $80k+/-). However, although $55.5k sounds like a very good deal, I strongly suggest rethinking the options on the car. It has: $3,070 - PCM 2.1 w/ Navigation $970 Bose $570 Chrome exhaust tips $490 Heated seats. $5,100 total I'd forego all of those for (in order of preference): $920 sport chrono $1,990 PASM (adjustable suspension) $1,050 Xenons $3,960 total And if you still have money burning a hole in your pocket, $2,100 Sport Exhaust $1,500-$2,000 19" Carrara S or Classic Wheels/Tires. I happen to have all of the options (some were standard) above on my Carrera S Cab. I think of the Cayman as first and foremost a sports car, and then a highway cruiser. So, on a limited budget, I would get options that enhance the driving experience rahter than toys or creature comforts. Nav is nice, but at $3k, that's a ridiculous price for a system that is 2-3 rungs down in ease of use compared to our Acura's. Heated seats in a coupe - hell, I only use them on rare occassion in my Cab with the top down. Never with the top up. Bose = big ripoff. The standard sound system is only average at best, but the extra money for the Bose barely improves it. Don't even think about the 6-cd changer. Chrome exhuast tips = purely aesthetic. The sport-chrono package is a must have in my opinion. The chrono part is more of a toy. But the sport part, with the enhanced throttle and braking response is a very noticable step-up in driving experience. PASM is also great if you are also going to be toggling between smooth roads where you want the tightest handling and rougher roads where you want to keep your fillings in place. It's probably not worth 2x the price of sport chrono, but it's still high on my recommended list. Xenons are a strong personal preference for me, scratch off if you don't care. The sport exhaust at $2k was the option I never would have ordered, but it came on the (in-stock) car I got a great deal on. Now it's one of my favorite features. Porsche doesn't claim any horsepower increase with the sport exhaust, but a friend with a 911S has had his dyno'd with it on and off and it shows about an 10+/- hp increase. In combination with the sport chrono, the sport exhaust feels and sounds like you put the car on a Barry Bonds steroid shot. Lastly, 19" wheels and the wider tires are certainly not necessary, but if you want that last bit of handling performance, that would pretty much cover it. I would NOT get them without the PASM, however. These are my recommendations from having 17,000 miles of experience with all of the above (and a few more) on my 911S. Obviously, do what you want, but like I said, the Cayman is a sports car and I'm guessing the reason the one you are considering is still around is that it has $5k of options that don't really add to the driving experience and a few important ones missing.
I'm sure others will assist you on the lease feedback. However, if I might ask, why are you leasing? By my calculations, you would be spending nearly $32,000 over 3 years to "rent" a car that would only cost about $52,000 to purchase outright (figuring the sales tax would be mostly offset by a 7+/-% discount off MSRP). Hell, why don't you just go the extra $20k and purchase it? Even at $650-700 per month instead of $800, you are still paying over half of the price of the car over a 3 year/30,000 mile lease. Unless there is an overriding reason why it makes sense to lease (100% tas deductable business expense) it doesn't make sense to me. And the way I look at it, if I couldn't afford to pay cash for my current 911S or previous Honda S2000, I shouldn't be getting it. They are a discretionary purchase, after all. Just my perspective, for what it's worth or not.
Regarding the 50 hp difference between a Cayman/Cayman S, to me, it would be very significant. That is slightly more than a 20% increase. I found a very "noticable" difference between the 911 and 911S - and that was "only" a 30hp and a little over 9% increase. You should test drive both, to determine for yourself if the difference is worth it. I had previously owned a Honda S2000 and from a purely psychological standpoint, would have had a tough time going with a $50k base Boxster that was noticable slower than the $32k, exceptionally well built Honda. The 2005 Boxster S (280hp) was slightly quicker than the Honda. That's not to say the base models aren't reasonably quick and let's face it, all Boxsters, Caymans and 911s have exceptional handling, braking, driving dynamics and feel - which to me, is still the primary reason to buy any sports car.
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