i have 2 mp3's that won't transfer to my ipod. at first, it said the operation device timed out or something like that. but now it just stops updating and doesn't add them. i'm on Win xp pro. any ideas whats wrong?
Try using the Convert to XXX feature in the Advanced menu of iTunes. This will create a new version of the MP3 in the format and bitrate that you have opted for as your import settings (in iTunes preferences). See if the new version will transfer.