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you should have no problem copying them over.. as far as playing the protected content you will probably need the license files or whatever ( dont know much about this cause i stay away from anything todo with itunes or mac for that matter! ) there are various ways to remove drm protection...

at the top of explorer just change your view setting.. it should also be available from the context menu if you right click on an empty part of the screen and select a different view option

over paranoid. each time you use flash, within a browser or whatever.. it makes a check to see if youre using the latest version, if not a popup will appear asking if you want to update. i got this popup 2 days ago or something so there you go!