Picking a top 5 is a very difficult undertaking, so I cheated and limited my selections to pre-war individual cards/cabinets (e.g., no team photos/postcards, press photos, etc.). And even then, this was a difficult task!
(1) 1873 Warren Studio CDV - Jim O'Rourke
(2) c1943 RPPC - Roy Campanella
(3) 1893-94 Perkins Studio Cabinet - Hughie Jennings
(4) 1898 Polensky Cabinet - Fred Clarke
(5) 1914 University of Michigan Photo Card - George Sisler
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HOF "Earliest" Collection (Ideal - Indiv): 244/342 (71.4%)
1914 T330-2 Piedmont Art Stamps......: 114/119 (95.8%)
1923 V100 Willard's Chocolate............: 177/180 (98.3%)