Welcome and thanks for sharing your perspective.
I always say CSC first. It is more expensive and perhaps less exciting to think about than than bolt-ons, but if you do that and decide on a lighter clutch + flywheel, you're gonna find it legitimately adding more "life" to the car.
Surprised Challenger was on your list. It's pretty different against this, the S2000, and your Cayman. I had an R/T rental. While an SRT would've made me happier, it was fun in its own right, driving around town in a loud....boat. Honestly that was fun, but holy hell gas costs.
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