Which Cayman would you do?

Grand

Brac is mostly for diving

The 911

Do you prefer power or being new?

Eta.

11k miles??
That's almost new and already took the big hit. I'd get that. Rarer, faster and much higher future resale.

subtle brag much

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$47K 2014 Cayman S, 11K mi.
3.4L 325hp

Or

$55K 2018 base Cayman 718
2.0T 300hp

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That is pretty easy the 718 (982 chassis). First, despite a higher peak HP the 2.0T will have much more area under the both the torque and HP curves and have more peak torque. The 718 is also a MUCH better chassis, the new Cayman S is faster on the same tires around a track than the prior generation GT4.

However, lets not fool ourselves nobody buys a new $55k Cayman, add up the options then revisit.

718, no doubt.

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subtle brag much

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Not directed at you— but why does everyone on here say ‘subtle brag’ when the correct term is ‘humblebrag’?

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I see base 718 with 59K sticker with avg selling price ad 55ish.

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A Porsche with only 3.5k in options is essentially a stripper, if that is what you want then fine. If you plan to use it as your main vehicle you might want to build one out and see what you really want/need in a daily driver. Porsche barely gives you wheels and tires for the base price.