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Adding wifi to the iPod itself would be cool, but also would have it's negatives, such a running down the battery (do you really want to share your music with the people on the subway if it's going to cut your battery time down to a couple hours?). And then there's the idea that it would make it even easier for you to visit a friend and let him download 40gigs of music (no cable necessary).
Adding wifi (and maybe even bluetooth) to the iPod's dock seems more sensible.