I have an iPod classic, purchased in 2008. I am running into an issue where when I add new albums to iTunes (not from the iTunes store or from an actual CD), only about half of the songs will make it on to the iPod when I sync. The songs all show up and work on iTunes, and my iPod is set up to add the entire library, but some of the songs just don't make it on there. The iPod isn't anywhere near capacity. I've tried adding them to specific playlists and although they show up fine on iTunes, they are just completely missing from the playlist on the actual iPod. Everything is up to date, software wise, so I'm hoping someone can offer some guidance. Thank you!