RE: Classic vs. New
To me it appears to be a matter of pride of having (or not having) a certain ride or the advancements that cars have made over the years. And some people just like to have control of something because they most likely have none over their job, family, etc. So I wouldn't take it seriously. In fact, you should create your own club and have people joined based on their love of cars not the year of one.
Jeremiah, I like your customization idea with the chrome. I was thinking about a custom paint job with a light blue pinstriping work (around hood stripes). Or maybe ghost flames. Either way, my mind has been going a mile a minute thinking of how I can make my challenger different from anyone else's.