I have discovered a bug in the iPhone.
I have some lists set up that look like this:
Rule: Song that hasn't been played in 2 months
Select 1 GB at Random
This rule is so that I don't listen to the same songs over and over, and I always have 1 GB of stuff I like on my playlist. When I drive back and forth to work, I listen to Podcasts, and at work I listen to my music. When I get home and synch, my iPod reports to the main music library what songs I listened to, so they get replaced.
However, I also sync my iPod between 2 computers - one just for music, 1 just for the calendar. This means that my laptop shouldn't put any music on my iPhone - just sync to Outlook. Only my home PC is my music source.
But - if I sync my iPhone to my laptop, then sync it with my home system, my "listened to" music doesn't get registered as having been listened to - the playcount remains the same. However, if I *don't* plug the iPod into my laptop for calendar synching, then my main music library gets the message that I've listened to a song.
I guess what I'll have to do is wait to get home, sync with my home library, then sync with my laptop, then sync with my home library again.