Now I know what you're thinking, the music is bugged. This is not the case however. The music will play just fine in foobar2000 and VLC, and show the correct track length. It is only iTunes that is having this problem. I've tried using the iPod plugin component for foobar2000 before, but I had really mixed results with it (such as all my cover art getting mixed up, or removed outright), so I'm not looking to try it again.
Search results do turn up results, but for errors importing CDs. These are albums that I have purchased directly from iTunes, and were on my previous iPod with no trouble. I'm at a loss. I figured I'd check to see if anyone else has had this problem before I go bug Apple Support.