I'm currently in the same market, and have it down to the same two cars. What somebody said about the Z being 85-90% of the Cayman at 50% of the running cost is absolutely right. During my rational days, I am tempted calling up the Nissan dealer. During my other days....
There's just something about the balance (and the sound) of a mid-rear engine sports car. It was a driving experience that was so incredibly unique and rewarding. But finding one that isn't 7 years old and is in the same price range is tough, and I'd really prefer to go 2009+ with at least part of a CPO remaining.
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And the OP is talking used, which is definitely a chick car. Though again, respecting his own taste buds and all that.
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I...don't even know how to respond to this one. The Cayman is, as stated by virtually anyone who has ever driven one, one of the best engineered sports cars readily available to the (relatively) common person. If that's the definition of a chicks car, okay. People need to stop living in the 'Porsche with panties' past. The Boxster (and thus Cayman) have improved leaps and bounds from the mid-90's, and if it weren't for Porsche's fear of cannibalizing the 911's sales, would be the best sports car in their lineup.
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The thing that pushed me toward the Z was the potential IMS (Intermediate Shaft Seal) and RMS (Rear Main Seal) problems reported on various Porsche forums
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Keep in mind, IMS is no longer a concern on 2009+ models.
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Unfortunately, $350 oil changes are not in my budget even though the Cayman has a 10k oil change interval which is crazy imo
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The previous timeline was, IIRC, 2 years / 20k miles, so 1 year / 10k miles is pretty conservative. It helps eat some of the oil change cost. What, IMO, is a bigger concern maintenance wise are the tires. But the biggest concern is, to find something in the same price range, the lack of warranty for something catastrophic. From most of the first-hand accounts I've read, Porsche seems to be fairly reliable, but no car is bullet proof, and those bullets cost a heck of a lot more to fix on a Porsche.