Cool idea
toughest one by far will be 1904
There is only 1 Allegheny Dummy Taylor card and it will be 4 figures if you ever locate who has it and if they want to sell.
Your list is similar to a type collector, but with your type of collection there will be some years with many many sets to choose from and some with none.
PS.
Like the great players you chose, Ike Boone, Hauser, Taylor, C.Mays, Pipp, Berg, etc. .........all are just as interesting if not more than most HOFers.