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The reason the coupes sell for less is because there are more than 3 times as many of them made. In 68 and 75 there were more convertibles sold than coupes, but in 69-74 there were always significantly more coupes sold than verts - sometimes 3 or 4 times as many.
I think it's more about drivability. When you were buying a "new" Corvette it was probably your daily driver, and convertibles weren't always desirable as DD's. Today the verts are more in demand because they spend more time in the garage than out in the weather. Even if I wasn't a purist I couldn't see myself driving the 68 to the office every day and sitting out in the rain, getting tree sap on it, etc. But I drove the 81 everywhere in all kinds of weather for years.
As a rule, I hate convertibles. They are noisy, hot in the summer and cold in the winter plus you always have to worry about damage to the rag top whether from the elements or someone who likes to cut.
As a DD I would take a coupe any day. To me the C3 is about the best looking convertible around. I specifically chose not to get a C5 vert because it's my DD. For a weekender car, vert's the way to go.
So, let's see, all the guys who own coupes are going to vote for the coupes and all the guys who own convertibles will vote for the verts (and I'm well over 40). An interesting point is that the base price of the 69 convertible was actually about 10% lower than the 69 coupe. That said, I'd opt for a vert if given the choice. I love my coupe but a roadster would be very nice. You're probably asking yourselves "Why "RagTop69" when his sig. pic. is clearly a coupe? My 69 Mustang is a rag top so I use the same handle on every forum for the sake of simplicity. I like the K.I.S.S. principle.
We have six people in our house (us and the four kids) and have three 2-seat convertibles - the '71 Corvette, Kim's '75 Triumph TR6 and her Boxster S. So our household is partial to convertibles.
I like both styles very much. I have personally owned 8 coupes and no convertibles. I like the uniqueness of the coupe. Those long sail panels just make the body so sensual in appearance. With the option of removing the roof panels and a removeable rear window, all of which can be taken with you, should you want to change the air flow thru the cockpit with different window/roof arrangements is just fantastic.
If I were to get a convertible, I would want it with only the hardtop option, in that configuration the car looks absolutely the best. The small vinyl top does not fit the cars beautiful lines very well, and in my opinion looks the worst when it's in the up position. I very much prefer the convertible with hardtop first and then with no top on second. It would be the only way I would own one.