Ooh, I have one of those! It is diddy and shiny. :D And yes, you do actually need iTunes I'm afraid - if you get it, it'll convert all your music to a format your ipod will play (You'll still have the originals in a format playable in WMP, don't worry! It just means you'll have a folder with copies in.), and all you have to do is drag and drop the songs you want into the ipod thing on the sidebar. It'll be fine! :D

(WORD OF WARNING though - as far as me and my sister can tell, it plays songs in the order you put them on your ipod. I know you listen to lot of operas and/or musicals, so I figured I'd warn you in case you like listening to them the whole way through!)