Honestly? I can easily see you driving a Camaro in the sense that there aren't a lot of stereotypes around them anymore. They, along with Mustangs, are like the blank template for cheap performance car in much the way a Civic is a car or an F-150 is a truck. Besides the usual criticisms you'll hear for Camaros and some complaints about visibility, I haven't heard anything too bad about this generation. You might want to give it a test drive. You never know.
The 996 though? I hear the upkeep on them isn't a pain like it used to be, but they're still not cheap, and I can imagine you wouldn't like that after a while. Know what European car brand I could see you driving though? Jaguar. Every Jaguar owner I ever met has a hint of old school "punk" about them. You strike me as the kind of guy that rocked denim, patches, and Docs in high school.