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Although I have a '93 40th Anniversary coupe, I wouldn't mind owning a convertible version of the same car. My second choices would be a 95 ZR-1, 96 with the GS engine, 88-91 Callaway Twin Turbo, and a '84 coupe. I guess you could say there isn't a C4 I don't like.
as long as it hasn't been butchered the year shouldn't matter much. The 84.... not a great car. Try to stay away from the digital dash, they are expensive and prone to go out. Also the 4+3 transmissions are not the best. I have a 96 and I love it. I had a 94 and an 84. Didn't much care for the 84. It was great when it was the first Vette I ever owned, but after the 94 I never stepped back in the 84.
A 96 Collector edition with a 6 speed would be a sweet ride. Probably be worth some money one day. Otherwise like another member said... ZR1 or GrandSport.
I bought a 90 ZR-1 because it was the most vette I could find for the budget I had to work with. I don't know for sure that the ZR-1 is for everyone though. There are too many "myths" out there about the car that are not exactly true or some are just false or some are over blown.
If I had it to do over with the same budget I'd still get a ZR-1 but I'd look for a car from a second owner that was a "hands on " type....ya get more ZR-1 that way...mine was from an original owner that was "hands off" and that cost me some coin. Time capsules don't make good toys unless ya just like look at them and not drive them. JMHO
GS's and the other special C4's were out of my budget so I couldn't do anything but look & dream. I'd say if you can spend over 25K for a C4 you are just starting to get to where the really choice C4's are.