For the past couple days, my iPod mini has been failing on me. There are no problems with it if I just want to listen to music that's already on it, the problem is in the updating.
When I plug the iPod into the computer, iTunes opens up and starts to download any new songs. It's really a coin toss as to whether the songs actually get downloaded. Usually, it'll start to add the songs, then hang once it gets to a certain point.
This happened once or twice before, but I was able to just cancel out, eject the iPod, and try again. If I switched from USB to Firewire, or to another USB port, it would work again. That method hasn't worked for a while now.
At the moment, I've tried just about everything I can think of. I updated to the latest version of iTunes, and I updated the iPod to the latest software. I did a full restore on the iPod just to be sure, and I restarted my computer before I even tried again. When I started it up and tried to hook the iPod up again, it started downloading the 900 songs... only to get stuck on 300 or so. iTunes wouldn't respond to a cancel, or an eject. I tried to force quit iTunes, and it made Finder hang too. So I had to restart AGAIN. At the moment, my iPod is disconnected, and still frozen on the "Do Not Disconnect" screen. It's been getting harder and harder to reset it when it hangs on this screen. And it does hang on that screen, every time, because iTunes never finishes updating all the songs.
I looked into this a bit, and the only easy solution I found was to remove all streaming files from my master library. I wasn't sure if that would work, and guess what, it didn't. The only other info I've been able to find tells me to DOWNgrade to a lower version of OS X, to a point where the software still worked. I have no idea whether I should do this, or if there are any other possibilities.