I spent the afternoon trying to synch my iPod to iTunes after creating a new iTunes Library. My new computer is so fast in comparison to past computers it is unbelievable. I use to have to synch my iTunes overnight because it would take 6-8 hours back when I had 70GB of music. Now that I have like 100 GB, my new computer can do it in 10 minutes. What troubles me is the fact that iTunes says it has a different number of items on it than my iPod says were synched to it. Can anyone tell me what is going on?
Sorry I'm not an iTunes expert. What I can say is, being a good computer and software user, Apple really doesn't want to make it easy to use. One time I did a confusion with my libraries and iTunes had all my music in my PC be DELETED. Just because the actual files did not match the list in the library. So iTunes had it take its own list as the "authority" of what "should be the right setting" then delete everything not in list. Since the library I created was blank, it began the comparison and, when I noticed it, I saw nothing more than the empty folders with artists names in my music folder in my PC.
iTunes can be really confusing even if you're tech savvy. Sometimes not everything is syncing, and there is no reason why. Like sometimes iTunes splits one album into two, even tho every info is the same in every songs. That's just apple's magic :p
try to update or put to the latest version your iTunes.
I suggest also watch some YouTube. I have encounter that also and do some bunch of research to google and youtube and it works for me.
It usually takes time to update. In my case it was 1.5 hours of updating.
As they say patience is a virtue.
I hope it work also for you and Good luck!