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For me it's really simple; I don't play to have the most loot, so if I'm running multiple shaman in a pug or with friends, then I roll once. Each shaman doesn't get a roll. If I'm bringing a multi class group,i.e; Pally, lock, mage, healer, sh priest, or any variation thereof, if the item is a significant upgrade, then whichever toon that can use it rolls. My multi class group has a lot of clothies and they all are wearing more or less the same gear, if the item is a big upgrade for all of them then they all get a roll.
If it's gear that I can't use or won't use, all my guys pass on it. With my guild the same rules apply.
edited for attrorcious sspelin