In terms of Hall of Famers, I would say that the Negro Leagues is the toughest category as many of the early players did not receive autograph requests and some/many were rumored to be illiterate. Here are pictures of some of tougher Negro related Hall of Famers in my collection. I have others such as Stearnes, Posey and beautiful J. Johnson letter you can see in my photobucket.
Dighigo signed letter to his son-
Willie Foster signature from his personal bible-
Effa Manley Signed Book-
Alex Pomez signed letter-
JL Wilkinson Signed Postcard, one of less than 10 known examples. This is from his Grandson, via Jim S.