k well xp is a different section b/c there's some differences in the way LW works with iTunes.
As soon as you connect your iPod to your comop it will update the playlists. I would recommend you update it manually. In the following link it has links to iPod tutorial which shows you how to do this & other things. There's also an iTunes tutorial & a link to iPod forum. Also there's some simple explanations & samples about how to get songs properly imported from LW to iTunes whilst using windows. See My iPod & iTunes importing (click on link)

Thanks to Stief 4 identifying the link error.