Did you try the general iPod fixes?
You don't have to tell anyone where you got your music from (for all anyone knows you could have ripped one of your CDs to your library)!! All you need to say is that you're getting errors when trying to add files to your iPod. Did you use the search on the Apple site? Their forum probably has a search function too... use that before you ask a question

It just sounds to me like an iPod issue rather that LW but someone else here might have more/different ideas. You could always have a look at iTunes support site too... just in case someone else has had the same problems or maybe the prob's related to iTunes somehow