On the used Cayman S vs the 370Z. I looked a the same idea. A really nice 06 Cayman S with under 9000 mi for $41000. After I drove the Z there was no way I would spend the extra 5 - $6000 over the deal I got on my touring/sport.
Keep in mind that the Cayman is getting a completely new engine for 09. That is part of the reason you see new 08's with $10k discounts on them. In that scenario you would be looking a $68k reduced to $58k in comparison to the Z. It then makes even less sense.
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16 Cayman GT4, Carmine Red, Buckets, PCCB etc.
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