I could turn the question around and ask why would anyone pay $55K - $65K for a used car when you could buy a new Cayman for the same money. Personally I don't like buying used cars and that is doubly true for used sports cars. I'm not saying that you can't find exceptional values out there, especially with the 996, but when I pay $60K for a car I don't want to have to be concerned that the car may have been abused by a former owner.