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Yes the Help action is only useful if the hit would be more damaging for the creature getting helped. Mathematically it would be something like this (I'm ignoring extra damage from the crit for simplicity, the doubling of only the damage dice make it complicated): Creature A would hit only on...

While in reality getting ganged up on from opposite directions really is a really bad position to be in and the optional flanking rule might even be realistic, I find that the it just :):):):):) all over the entire 5e system. -Got a group with few frontline fighters, or even worse, one tank...