I think there are a vast set of rules that directly affect the play of the game - and these should be enforced 100%.
Then there are those rules that don't affect the play of the game as much as they affect the flow or administration of the game. These are the rules for which we can be strict only when necessary, and lax when it calls for it. Coaches out of the box, batters taking signs from out of the box (in suck rulesets where this is applicable), coaches wearing gear to warm up pitchers (I would enforce this 99% of the time, but when Johnny lob-ball is coming in to just get through a game, I think it may be acceptable to let this slide), stuff like that. Enforce if it's causing you a problem, or if the coach is a jaggass. Let it go when it truly doesn't matter.
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"Many baseball fans look upon an umpire as a sort of necessary evil to the luxury of baseball, like the odor that follows an automobile." - Hall of Fame Pitcher Christy Mathewson
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