2 sports in consecutive seasons, perhaps. (Football, then basketball, then baseball)...
Starting football & volleyball at the same time... that would be more difficult from a rules mastery standpoint.
A quick example of "knowing the rules as an official" vs "knowing the rules as a player": why does the kicker kick the ball into the ground in the vast majority of onside kick attempts? As a player, I had no idea why we did that... once I started reading the rulebook as an official, I read the free kick rules and had the lightbulb "A-ha, that's why it's done that way" moment.
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