I personally have not done this, as I have a server at home where all my content is stored, and I just sync the laptops with it, but I think since XP (perhaps earlier, but I don't remember), Windows has had the File and Settings Transfer Wizard (though I think it's called something else in Win7). That should copy everything over for you, provided you don't do something like create new folders in the root directory. I would expect that the Wizard would not find those, but if you use the standard folders (my documents, my music, etc.) it shouldn't be a problem. I'm pretty sure this can be done over a network, too.
I do not have my trophy yet but I am an avid zune hd user and I can tell you that the zune software is very easy to transfer from one computer to the next. I can plug my zune hd into a different computer that my zune is not registered to and copy all of my music to that computer. I don't have a zune pass yet but with the zune pass you could easily copy everything. I'm not sure exactly how to answer your question so ask anything you would like to know?
Whitney, SWEET! Kudos.
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