iTunes and Windows Pocket PCs?
 

TunesSync for Windows Mobile is a simple, yet powerful app that allows you to copy your favorite iTunes playlists to your Pocket PC.
Download it here. for $9.95 @ 90 day Risk Free Guarantee on two computers. I think it's worth a try. Get a big & juicy Micro SDHC Card and you might retire that iPod. Keyword on "MIGHT".