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Lets just say what if 1 day your pokemon can hold 2 items in theory what would you use? For example on my emboar id use expert belt and quick claw=first attack+more likely crits.
Hmmm I don't think I would want my pokemon to hold two items. It would give you a better chance of winning if that was the case, and I prefer a challenge.
Since this thread is leading to a "What if" for more than one specific Pokémon game, your best bet would to drive the discussion over to Pokémon Gaming Central.