I don't see cars like that ever achieving the status of the '67/'68 GT500s.
First, they built all of 3,590 GT500s both years, both body styles, all options. By Contrast they built 19,140 '03/'04 Cobras. Rarity simply isn't on the side of values skyrocketing.
Second, you also have to consider that expensive as they were new '67/'68 Shelbys were not thought by those who bought them to be something that would appreciate in value. After 15-20 years they were just old cars. What eventually happened to old musclecars had never happened before in terms of collectability driving crazy high prices decades later. A big part of that was that the Baby Boom generation, which was much larger than the succeeding generations, retired with great pensions and savings and used some of that to buy their high school dream car. The people who will be retiring in 20-30 years don't have those gold plated pensions. People will be working longer, living longer, etc. and I don't think the math is as advantageous for future generations in terms of being able to make a large purchase based solely on sentimental reasons.
Third, the perception of future collectability means that though in the minority there are fair number of '03/'04 Cobras out there with almost no miles on them, sitting in climate controlled garages waiting for what their owners perceive as the inevitable enormous appreciation that will allow them to cash in big time. Sure, some of these cars got raced, some got and will continue to get wrecked, but those perfect examples in hibernation are going to depress the values of the drivers that are left. They will be like a barn find, but the barn was climate controlled, free of pests, etc. and there are a lot more barns. Sure, people will see those cars sell for $150,000 in 30 years on Mecum, etc. and think their clapped out driver must be worth $100,000, but what is the market really bringing? Assuredly much, much less, because people aren't stupid. They know how much its going to cost to try and turn that ragged out driver into a show car. Parts availability, labor costs, and the complexity of those cars being much greater than the '60s cars is all going to factor in.
Fourth, I'm sure at some point they will be worth more than they are now, BUT you have to look at the value of money over time. Inflation means a lot, because there's a theory that crazy price fluctuations aside, in general commodities don't actually appreciate in value over time; they just keep pace with inflation. So, sure, the number of the selling price goes up, but what's the value of money done? Its only going to go down in terms of purchasing power.
I've seen this happen in another market. I've collected and read comic books for years. Starting in the '80s old comics started selling for a lot of money. All the rare stuff like Action Comics #1, Detective Comics #27, etc. This caused people buying new comics to start saving them, treating and storing them better. By the mid '90s the comic book market was 5 times its normal size. The old stuff was selling for hundreds of thousands to millions, and this drove buyers of modern books to not even read them. They went straight into bags and were stored in climate controlled places to avoid discoloration, etc. The comic publishers took advantage of this selling books labeled as "1st Issue: Collectors Item!" and books pre-sealed in polybags, sometimes with trading cars, multiple covers, foil covers, hologram covers, etc. Prices also went up to where most books were in the $2-$3 range where a couple years before they had been $1, but the paper quality also went up (no more newsprint) and the coloring became epic, as did the art.
That was all well and good until the early '00s when the bottom fell completely out of the industry. People found out that with rare exception those books they'd saved were no longer even worth their cover price because there were 4 million near mint condition copies for sale on eBay. The days of speculation were over and a lot of boxes of comics are still in people houses waiting for a market rebound that most assuredly will never come.
I digress into this to illustrate that collector markets are fickle, and that past performance is not indicative of future success. With limited exceptions collector items be they cars, comics, or baseball cards need to be purchased for the right reason; personal enjoyment. They are almost never a sound purchase from a financial standpoint. If I added up all the money I have in my '67 over the years I'd be lucky to break even on it, much the same as the fact that tough my Wolverine #10 is worth north of $100 most of the collection around it is worth less than I paid for it. I keep my '67 because I love it. I read comics because I love them. The only time money enters the equation is when I decide if I can or should afford something in those realms I want. So a "wise" purchase, most assuredly no. A "good" purchase? That's in the eye of the beholder, and something only you can decide.
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