I'll say this much...
Speaking for the generation after yours, I must say that things are a little harder today. Cars cost 10 times as much as they did 30-40 years ago, houses the same thing. Incomes are up too, but I can't say that they're up 10 times as much. My father got his 'Cuda for somewhere around $3,500 and went into the Military, where he paid $0 for tuition. I bought my first car for $27,000, and have over $40,000 in tuition debt. My wife is paying $8,000 for her first (used) car, but has over $60,000 in tuition debt!! Our income is close to $70,000 annually, which still just barely pays the bills.
I had to penny pinch to buy my 'Cuda. In fact, if I hadn't found the one I did at it's 11,000 price tag, I wouldn't have one today. The next cheapest price I found was $9,000 for a rusted body of a Cuda - no interior, no motor, trans, etc. The next price UP was $25,000 for a 340 'Cuda in only slightly better condition than the one I bought. I pretty much skip over the section at Carlisle with $100,000+ price tags.
Eventually, the prices on these cars will dip down into the range that my generation can afford. They'll start getting snatched up again when we realize that we can afford them. It may take quite some time, but eventually, as we progress into our careers and the like, they'll rise in value again. However, I see things like fuel prices becoming a big concern for everything, especially the classic collectors market. Eventually there's going to be no gas. And when there's no gas, 440's and 426's and 528's are going to be pretty much useless. These cars will drop into 4 digit-prices so that the people who can afford to transplant a Hydrogen power plant or God-knows-what engine into it can do so.
I was actually just thinking the other day that I'd like to pick up a "General Lee" year Charger (not an actual General Lee, but that year/body style.) Of course, the recent Dukes of Hazzard movie ramped up prices on those cars by trashing like 30 or 40 of them...
Jeff