If you buy CPO from a dealer, they come with 2 year/unlimited mile warranty. Not sure whether you're shopping recent used, new, or older Caymans. 997.2 will not have CPO because it's beyond the time limit. CPO is a great deal if you're shopping for one year off lease trades, as it adds two years to factory warranty and has unlimited miles. So you effectively get a five year unlimited mile warranty.
My experience with Porsche (and everyone else in my orbit) has been fantastic. Zero issues. Parts cost roughly similar for those two models... ie, a set of brakes is more than brakes for a Honda, but you're getting the performance and the stuff lasts as expected. Maybe a fuzz higher for the 911, but not enough to really worry about I would think. A flat six Cayman is going to be a higher spec model, so parts cost isn't the same as the 4 cylinder models.
The dealer service groups are very good, from my experience. IE - typically at a Honda or Ford store, some of the entry level techs leave something to be desired. The Porsche techs have all been very respectful, good communication, fantastic service. Same with independents, most of them are enthusiasts who care about the cars... the cars aren't an appliance to them.
997.2 is naturally aspirated so you don't have the question marks of turbos. I believe that generation also had the bore scoring issues sorted out. 997.2 also fixed the IMS bearing issue.
Don't let parts cost/ownership cost drive your decision on a splurge purchase... if you're thinking about parts cost when you drive it, you'll be miserable.
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