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I think Steam keeps a record of what you've purchased, or at least I do notice when I look at the game / DLC catelog, it'll put a little "On Wishlist" or "In Library" as the case may be.
So yah, if you buy something you don't have already, it ought to just add it, no problem.
What I don't know is what happens when you've bought, like say, 5 items already, then you want to buy a discounted bundle of, say, 15 items, and 5 of those are the 5 items you've already purchased. Does it pro-rate the discount to the remaining 10? I don't know.
That is a good question.
I know Steam can integrate complete games you already own, such that you can launch them from Steam, but I have no clue regarding DLC.