Wow still very new at this site but have been spending countless hours reading up and waiting for my Gen 2 to arrive.
It seems that Gen 3 and 2 owners bicker so much it's funny. Both cars are very different in appearance but still come from the same womb. The reason I got into Vipers was because my friend has a Red 06 coupe and took me on a Viper run to Palm Springs here in CA.
The cars were unbelievable but my heart skipped a beat when I saw the Gen 2. They ARE a work of art but that does NOT discount the Gen 3's looks either. My friend who owns a modded up STI, loves the Gen 3 and continually scratches his head on why I chose the Gen 2. (backhanded compliment?) j/k
The revised generation is certainly the better car stock and can easily be modified to produce more because it is more technologically advanced. However I would seriously refrain from selling a 1996 GEN 2 because of what it is. You may very well end up regretting this decision because it represents the beginning of the GTS era which sparked the worldwide interest for the Viper. The car was just as revolutionary as the 92 RT/10.
The Gen 3 is a more sophisticated, powerful and beautiful (matter of opinion) in other people's eyes but a Gen 2 in my opinion just has a timeless look like the Audi TT, Lambo Countach, F355, Testarossa, Ducati 916/996/998 which envokes Passion. Red is a beautiful color on sports cars because it just exudes passion.
If it is one or the other, test drive the newer generations (3 & 4) and ask yourself which one you will be happier with. In addition, you can always have the Gen 2 sitting and you can drive it far less but still be able to enjoy it and it can bring you lots of cash in the future.
I believe the reason why people defend and argue the Gen 2's looks over the 3 is because there isnt much more to argue aside from it's looks but for the people who like/love the Gen 2 more based on appearance, it's like sacrilege to say they are comparable because it truly extracts their passion when looking at the car. Kind of like weak in the knees when I see the Bugatti Veyron always parked on Rodeo drive.