In the absence of a Speedster (which would be my first suggestion), I'm going to join the Cayman chorus. Buy the best one you can afford, hang onto it, and spiff it up with wheels/tires, springs, etc. as money/time allows. Get the 6-cyl, and get the manual trans.
It's a small enough car to place on the road in the mountains, the steering is razor sharp, and going fast is not a big effort. The cabin is big enough for me, when even a C8 feels a bit tight.
Working on them is not something I'm interested in, but that goes for any modern vehicle, so there's that.
I don't think I would ever be satisfied with any of the choices, however.