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It is tough to make a recommendation.
In my case my wife made all the same comments except she said you love the old one... just buy a new one...
My DD sits outside even in the winter...
It is a small price to pay to keep a classic and play with a current.
We have recently discussed it again, because of the time it takes to detail all 4 cars in our 2 person family and my wife again has said don't sell it...
This is an easy fix. Go out and find yourself a nice c5 and make sure the wife loves it. Then take the difference between the price of your c5 and what you would have paid for a c6 and build a seperate garage in the back yard for your c3. This would also be the perfect time to get all the tools and the lift to put in your new garage. Everybody's happy.
From: In a parallel universe. Currently own 2014 Stingray Coupe.
C7 of the Year - Modified Finalist 2021
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If it were my choice to make, a new C6 or a near new C5 would be in the garage. It is light years ahead of the C3 in terms of comfort, ergonomics, ride, power, economy, etc.
I had a silver 82 that was a beautiful car to look at. However, it did not have a manual transmission. I thought I could learn to live with it. That was a big mistake. I grew tired of the car because of the automatic and enimic performance of the "Crossfire Port Injection". Sold the car and went German for a while.
Today I have a 04 Z 06. It is hard to believe they are both called Corvette. Difference of night and day in ride, comfort and looks. Performance is not even in the same universe. The Z 06 is a rocket sled. Do it, you will not regret it.