I'm not a mechanic and I don't play one on TV, but... I was shopping Cayman and Boxsters used before i purchased the Z. They are absolutely wonderful to drive and can make very good DDs too.
I did some research and lurked on Cayman/Boxster forums a bit as well. They are not bullet proof,and with all respects to Ferdinand, have had some costly design issues that lingered through several model years like the IMS bearing issues.
Shop rates at the Porsche stores are in the $125-$180/hr range for labor, so for me it didn't make sense because the difference in performance is such that I'd need driving classes to realize it.
I'd never say it's not worth it to someone else, because only they can make that decision, and both are performance bargains in their own right.
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