You are correct in that older people want to collect cars from their youth. Basically, the cars they couldn't afford at the time. Personally, I just like to collect "neat" cars. I began driving when I was 8 on a tractor. I would have learned at 7 but couldn't reach all the controls. My mother started teaching me to drive a car at 12 but learned right away NOT to tell me to miss the pot holes on a beat up country road.
I'm trying to wean myself from old cars. Everything I have right now was made in this Century. Well, sort of, the Cadillac is a 2000 and that was technically the last year of the 20th. On the other hand, I've titled and plated around 250-300 cars so far in my life. (Not counting cars bought for parts.)