Prices of collectibles is a well studied subject. In your example the car prices are rising as the older men now have enough money to pay for those items they wanted in their youth. This will reach a peak and as you suspect prices will crash as that generation dies off. Then prices will remain low for a long time until scarcity will drive a small rebound for a few select items. I tried to look up some of the studies but I can't post a link yet anyway. In my case I've got a boatload of Heathkit electroncs that's in the long low price phase. Oh well.