For some reason I could see you in a car like this, wearing a pilot cap with a scarf blowing in the wind.
http://www.autotrader.com/cars-for-sale/vehicledetails.xhtml?listingId=428012081
Really for comfort and all-aroundedness I would say an 05-10 Mustang GT, but I don't think that's really a "you" kind of car. They are comfortable on long drives though, and easy to maintain. Slap on an axle-back, drop the top, and enjoy them sounds.
Like you said, S2Ks are completely meh unless you're driving at the limit. I've driven a couple and they bounced me all over the place on Ohio's amazing roads. Would not buy.
Have you thought about Z3s or Z4s? M3s? I know nothing about them, but they're options. Same with 350Zs.