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Some of the checks that are more common to fail are not having enough starters (I believe you need min 4) and making sure you actually have reliever roles set (have to actually set a primary role for them, not just have them in the bullpen. Again I think you need a min of 4). You also need to make sure your lineups are filled (or mostly filled - I forget if you need all 9 slots or if the check fails a bit below).
But most likely it's the way you have your pitching staff setup.
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