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With that said, I think your idea of test driving both is a good idea.
You've generally identified the pros\cons, they are just somewhat different cars so honestly I think it may ulitmately come down to HOW you intend to occasionally drive it.
Don't compromise by getting a slushbox for your wife, teach her to drive stick.
Between the 2, for me, the Vette. Although as I have posted many times, you can pick up a C5 convertible with a 6-speed for way less money, and while the C6 is a technically better car, IMHO the C5 is better looking, and from a performance standpoint more than good enough.
The heavy weight of the Caddy is not something that can really be redeemed by horsepower.
For the money you are throwing around here, though, IMHO there are way better choices. Older Corvettes in excellent condition that will go up rather than down in value, and are still pretty fast cars, old Jaguar XKE if you can deal with Lucas the Prince of Darkness, Lotus Elise that will go round a track with as good a time as the Z06 with way less HP (and fuel burn). All sorts of 911 Porkers. E30 M3, old M6 or 635 CSi, etc. etc.
You could buy an excellent E30 M3 for you and an excellent 450 SEL Mercedes (automatic, convertible) for wifey for less than either car you are considering, and neither one is depreciating now.
With regards to the Elise, while it does get better city mpg...the Z06 is right up there with it on highway mpg.
I love the looks of the Elise and know it handles well but I've never heard of them being anywhere near a Z06 on track times unless you are talking modded or a tiny track.
I'd probably go with the Caddy....cause, you know, I'm a family man
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