im a real fan of zen products and itunes, so i found a compromise. I know you probably are concerned about all your musc and how many cds it takes to get it over to windows media player, but theres an easier way. all you have to do is go into your itunes folder and reformat your music to a format windows media player will accept. There are alot of file conversion products out thre, alot of them free or having a trial period. i dont remember what program I myself did, but it converted 15gb of music fine. try getting it from download.com or tucows.com or something. good luck!