Because of the way the current trade system works, I think you would need to add features on both sides of the auction.
The buyer would need the "Buy 1," "Buy 10," and "Buy select number" options, but the seller would also need a toggle for the allowance of "Sell each at." This way, it is up to the seller if he is willing to sell the items individually or not.
Codewise, I don't know how feasible it is, but it's an interesting idea.
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