Everytime I lay into the throttle, I think to myself: "damn, this is a lot of fun for $36k!".
Do yourself a favor and DON'T test drive the Cayman. I did, and seriously considered stretching, but I would be eating into the cash earmarked for the improvements on our home we just bought.
If you're coming from a 280, you'll love the 370Z - it's a bit rough around the edges, but a lot of car for the money.
My other end of the spectrum was the MazdaSpeed 3 and GTI (did you know these come with a dual clutch transmission?), but fully optioned out, the 370Z was only several thousand more (minus 2 seats).
If you're shaking your head at the price of a P-car, even used, I'd drop the crosshairs down a notch.
Oh, my dream watch is a Patek, but I own a Seiko chronograph that I bought on sale.