Thanks again bro, I noticed the depreciation as I saw so many of them in the mid 30s, it was kind of shocking, but also very much appreciated. How tall are you by the way? and how was spacing in the cabin on any long trips etc.
Cabin was perfect for me at 5'8" and 150lbs. I sold it to a guy who is around 6'2" and 200+lbs. and he was comfortable with the driver seat all the way back against the back of the cabin. I would say its probably not a great car if you are heavy set or really tall as the cabin might get really tight. I had a 2010 Shelby and that thing was huge inside, in fact I owned both the Cayman and the Shelby at the same time last year and ended up selling the Shelby because it was just massive and I didn't get the same feel and connection to the road as in the Cayman. Part of that may have been the mid engine layout of the Cayman vs the Shelby, but it felt like a boat every time I drove it and then got back inside the Cayman. The Everyday Driver youtube review I posted a few pages back pretty well sums up the Cayman's driving characteristics, you really feel one with the car and the road and literally every turn in that car inspires confidence that you can do almost anything and retain total control over the vehicle and road. That car makes you feel like a superstar with each successive turn. The Shelby was just a monster going from light to light in a straight line or when merging onto highways, but in the twisties I felt little to no confidence that I could keep the rear of the car from flying out from under me.
For such a small 2-seater sports car, the Cayman actually has a surprising amount of storage space in the trunk and front (frunk) so traveling with bags for a weekend trip with a girl was no big deal. If you can get to a local Porsche dealer I would see if you can sit in a few Boxsters and Caymans to get a feel for the cabin space. Also at your price point I would also consider a 1-2 year old Jaguar F-type, M3, or Vette as all 3 would offer more cabin space than the Boxster/ Cayman and you could likely pick them up for around the same price. Tough choice man, but I don't think you can go wrong with any of these!