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If this is going to be your fun car & not a daily or practical needs car, definitely go for a Cayman, any generation! This is what these cars are meant for.
For canyon driving, I would prefer cayman over 911. I have driven 997.1 911 on SoCal canyon roads & had to drive fairly spiritedly to get the lighter front end feel. 911s, I think do better than Caymans on a track.
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