I have a 30 GB iPod Video that recently seems to have developed a strange problem. Whenever I connect it to my PC, it opens iTunes to synchronize, but iTunes does not receive the latest information from the iPod. For example, say I played a particular song five times since I last synced - this information is no longer being updated as it used to. Off the top of my head, the affected fields appear to be Last Played, Play Counts and Rating information.
I am able to successfully sync new content from my PC to my iPod, but information such as recently played, play count, etc. is not being counted. After doing a bit of research, it appears that the problem lies with the iPod, as the "Recently Played" smart playlist is not being updated once a song is (completely) played, so that would explain why iTunes is not updating accordingly. I have the latest version of iTunes and the software for my iPod. I did a complete restore of the iPod and this solved the problem - for one synchronization - before it stopped working again. From a similar post I started in the Apple forums, I'm not the only one who has this problem starting with iTunes 8. If anyone else has this problem and/or a solution, please let me know...thanks.