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Jason LI want to make sure I follow what you're saying...your supposition is that if all the fans from 2 given eras are both largely now deceased, and the supply of cards from each era is roughly equal, then the contemporary collector with no first-hand experience with either era, will choose the oldest cards as the favorite to collect?
If I understood that correctly, I think I could agree with this thinking. It would be the "perception" of scarcity because of relative age, I suppose, that would drive the increased demand for the older cards....
but you will likely still see favorites in both eras, and those who will prefer the art-deco style of the 30s cards over the tobacco issues, and vice versa...
Jeff,
there's nothing better than a hobby that is rewarding at lower prices! 
are you buying raw or graded? have you found better supply of one over the other?