Concerning the car show in which you entered the reproduction Cobra, it should not have been in the same category as the Bonneville. This should have been obvious when you registered the car and was the fault of the registration staff, not you.
The simple fact is that most of the people running your local car shows are not knowledgeable about cars, if not downright ignorant about them. Most of these local shows are run by well meaning folks that are trying to raise funds for some good cause or organization. As a result, they aren't full of car-savvy people.
It is unfair to someone with a vintage car (you didn't state how old the Bonneville was) to have to compete against a reproduction of a vintage car that may be only a few years old.
My favorite little local car show, which is run by a men's group from a local church close to my home, awards a plaque for "Most Original Car". They awarded it to a very nice 65 Corvette. The problem is that there was a small tag affixed to the console that stated that the car was "Restored by John Smith Restoration Shop". Also entered was an extremely nice original, unrestored 66 Pontiac Lemans. A "restored" 65 Corvette beat an unrestored 66 Lemans!
Now to address your two questions.
First, the older gentleman was upset at what he considered a miscategorization that put him at a disadvantage. Had your car been properly classified, he probably would not have been upset. There is a fellow that shows up at the same local car shows that I do. He has a vehicle that would compete against my El Camino. We enjoy good conversation and friendly competition because we compete in the same class.
I have entered Crimson Pearl in a few local shows, not with the idea of "winning", but primarily because most people have never seen an XLR in person, or have no idea of what it is. Quite frankly, most of the local car shows award "Top 25" plaques in addition to the other awards, in an effort to send more people home with an award.
Second, I would enjoy a win over another vehicle if they were both properly classifed as in the category. I would enjoy it if Crimson Pearl beat a current generation Camaro, Mustang, Challenger or Corvette. It would be a hollow victory against an original and unrestored Chevelle or 442.
MY moral of the story is this. I enjoy participating in the local car shows because I know that many of the people there have never seen an XLR, or at least never seen one close up! I enjoy answering questions about it. Same with my EL Camino. I enjoy the opportunity to meet and talk with folks about it and other cars from the same era.
Enjoy driving your replica Cobra, meeting new people and answering questions about it. If you get a plaque or trophy, great. But if not, you still take home the BEST trophy, you get to take your car home!
