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I’ve owned multiple of both, it’s Cayman all the way for me. Especially compared to a 996 cab which is easily the least loved modern 911 (just look at the prices). Comparing the two the Cayman will have a nicer interior, better more tossable handling, more practical storage, better MPG, likely better feature content, and IMHO much better styling. The 996 will have the edge in straight line performance but that’s about it.
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‘07 Mazda RX8
Past: 911T, 911SC, Carrera, 951s, 955, 996s, 987s, 986s, 997s, BMW 5x, C36, C63, XJR, S8, Maserati Coupe, GT500, etc
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