You might want to consider which players you would like to see represented in your "set", then pick the 2-3 cards of each player that you like and see how the years play out. There are certain years where there are a number of iconic cards and others with fewer, and you wouldn't want to end up with a "set" that did not include, for example, at least one Clemente or Aaron or Seaver.
Another consideration is whether you will limit yourself to the main set or include inserts or smaller sets (like 64 Stand-ups or the Supers from the early 70's. Many of these are also very cool and might help you include a wider variety of players.
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