How about a crafter's raffle, where the prizes weren't random items, but vouchers and coupons for a guild's wares that they already have in stock. That way winners could pick through a selection of items their level, or commission an item to be made on demand if their prize was large enough. Good items to offer on demand are enchanting rods and resistances, lion bags, +1 and +2 rings, things that are generally of use to all classes and levels. So even if there's absolutely nothing they like in the crates, they could maybe get a better shine on their sword or some weight off their back. I would like to see those, raffles based on enchantment rods or bags.
The idea of having 100 random items with 100 random rafflers without regard to level or class restriction seems far more hectic. If the low level participant wins something way over his head that he can't use and he can't even sell it, it's not really winning, is it? Same if an epic level character gets something iron, or a wizard gets a greatsword. Everybody could use a bag or voucher though. Plus in some cases this could generate the crafter revenue, since some vouchers might be less than the item the player wants; he can pay the difference with his own cash.