For days - Days, I tell you - I have been trying to update my iPod Shuffle so I can listen to the rest of an audio book (The Alchemist, by Paulo Coelho).
It's a long story, Days long. Apple put out some software updates which change the way the Shuffle is updated. Now the software that updates iPods is included with iTunes. It used to be a seperate piece of software called the iPod Updater, or something like that. I updated various pieces of software, more than once, and probably in the wrong order. Then... my iPod Shuffle would not update and iTunes told me it was corrupted, or it couldn't find the files it needed, or it just plain wouldn't recognize the shuffle (as if it wasn't plugged into the USB port).
I tried the 5 Rs as suggested on Apple's help information (reset, retry, restart, reinstall, restore). I was able to get to the Restore step a couple of times, but the restore step always failed... the progress bar just kept going and going and going, like the Energizer Bunny.
I ordered a new iPod Nano, for lots of $. Then I read a bit of information which implied that the iTunes library files might be the problem and I should restore the library to an older version. I did that, and then restarted my Windows PC with the iPod plugged in. When I started iTunes, it recogized the iPod and filled it with random songs from my music folder.
But that wasn't good enough for me. Oh no, I still wanted the rest of The Alchemist on the iPod. When I tried to add switch the random contents for the audio book, I ran into the same problem again! This time it ran out of space and started giving me error messages.