Your iPod software can be out of date. All you have to do is to select restore iPod to factory defaults either in the iTunes program or on the iPod itself. This will restore the iPod to the original factory condition. A word of caution is that you will loose all of your songs as they will be erased. If your iPod is still not syncing with iTunes on your PC or mac, then I suggest rebooting both the PC and iPod with the usb plug disconnected. Once the PC is back on and completely booted up, plug in the usb cord on the iPod and iTunes should pop up and you should be able to sync your iPod to iTunes Try to reboot the iPod and PC a few times if necessary, it should work.
http://pcfix411.com/downloads/doc_details/19-mp3tag Mp3tag is a powerful and yet easy-to-use tool to edit metadata of common audio formats where it supports ID3v1, ID3v2.3, ID3v2.4, iTunes MP4, WMA, Vorbis Comments and APE Tags.
It can rename files based on the tag information, replace characters or words in tags and filenames, import/export tag information, create playlists and more.
Mp3tag supports online database lookups from, e.g., Amazon, discogs, or freedb, allowing you to automatically gather proper tags and cover art for your music library.