I appreciate all the feedback, thanks all. I didn't expect so many responses!
To clarify the "image" aspect, it's not necessarily that I care what other people think, it's more that I care about the ramifications of what other people think. There's a slight but important difference. It's not a huge issue, just one I'm taking into consideration.
As someone mentioned earlier, I think it does boil down to what I like more - what will be more fun/enjoyable. I think once I drive the corvette it will make my decision easier. If that doesn't I'm in big trouble. I don't plan on ever going to the track, nor driving like a maniac on public roads, so I'm not sure the performance difference between the two is too important.
I've considered getting a sports sedan like several have mentioned, but I just prefer the look of a coupe. The Cadillac is an amazing car for the value (I'm just not a fan of it's exterior). However if the corvette had the caddy's interior, I wouldn't have any problem deciding. That's what boggles my mind about the corvette... GM clearly has the ability to put quality plastics and finishing materials into a car, if they want to. A new Chevy Malibu has a better interior than the current corvettes - it doesn't make sense.
I've considered BMW's and have been in a couple M6s. They are great cars, but for some reason I just don't find them as appealing.
I'm 29 now and it's interesting how your tastes change over time. If you asked me back when I had a camaro what to get, I would have said corvette in a second.
(looking at a hardtop jdbecks)