I was torn between a 996 TT and a Cayman S. For me it came down to the amount of money I wanted to spend. The acqusition prices were close, but I figured it would cost me *at least* another 20k in maintenance over the planned 7 years of ownership. Plus the looming prospect of an $8k tranny bill...etc, etc. A 996 GT3 is NOT the same price as a new Cayman S. They are more expensive, all things considered.

If I could justify the cost, there is no question that a used 996 TT or GT3 is a better "value"...but they are still too expensive for me. Unfortunately.

After driving around in my brother's 997TT, I found the 996 interior to be dated, also. The fact that the Cayman shared so much 997 DNA was attractive.

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2007 Speed Yellow Cayman GT 2.7 (retired)
2008 Guards Red Cayman GT 3.4
"Carpe Cayman"