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I recommend you get a 987.2 (due to steering feel and gearing, someone like you can solve the brake feel). With two sets of wheels, a base Cayman would be a wonderful commuter. It's also the "good"/closed deck 9A1 engine but the only one without DI, so no carbon cleaning ever. Only downside I can think of is passenger side rear three-quarters visibility in odd merges.
Interesting on the wind noise. I don't hear any, even at higher speeds, on the highway with the Boxster. I never noticed an "increase" in wind noise going from 911/Cayman to the Boxster.
The squeaks and extra moving bits are certainly there. The Cayman actually has more engine noise due it being "more in the cabin". Finally, both have a solid amount of tire noise, some of it by design so you hear the surface. The car can be whisper quiet on new blacktop and roar on some concrete. You can pass a sprinkling of loose surface and hear the pitter patter of it hitting the wheel wells.
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