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Marc S.Kevin: Your points are valid, and your questions make absolute sense. My methodology certainly leaves a lot of holes/problems with executives and other game officials, and I by no means suggest it reconciles those holes.
Perhaps I am just prejudiced against modern cards? Nearly ever modern player, official, or anyone else associated with baseball has had a baseball card produced at some point after 1980. Thus, they fall from legitimacy in my eyes. If George Hildebrand made the Hall of Fame at some future point, I would never look at his 1993 Conlon card as a "hole" to fill a HOF collection.
Perhaps if I refine it like this: If a player has a card produced contempraneous to his career -- that should be considered a legitimate card. Outside of that, it should not. So an umpire who was active in 1990 should be able to use the T&M Umpire cards. But this then necessarily excludes issues like the 1961 Fleers, the 1993 Conlons, any of the TCMA cards, and any of the cut-up game-used stuff of yesteryear's stars that current manufacturers shove in packs of product.
Thanks for your points.