Between a brand new Z and a slightly used Cayman S, my recommendation is to go with the Cayman S "IF" you are willing to confront possible high maintenAnce/repair cost. Don't forget that repair issues will only be issues "after" the warranty period.
I am sure you know about Porsche CPO warranty so I don't think you need to worry about repairs for a while.
Drive them both again and go with your feelings. I drove the Cayman myself and fell in love with the driving experience --- i didn't buy one though as they were out of the DI models.
Trying to get input from Z-owners from a Z-forum may not be your wisest move. So bear with a cusations.
Good luck to you.
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