HELP! Ipod sync not performing properly. What can I do?

Question

Yesterday, when I clicked my Itunes icon on my desktop a message came up about some kind of update. Itunes was going to be loading new formats and I was asked if I wanted to keep files sorted. I clicked yes and then continue. I noticed it was doing all kinds of crazy stuff, so I stopped it. Now, I have songs missing, album artwork missing, songs that were supposed to be deleted are back, songs won't play all the way through on my ipod, and MOST annoying of all my ipod is not synching properly. It will get stuck synching random tracks and will just stay synching that one track forever. When I unchecked the songs the ipod was getting stuck on, it synched OK for one disc I'd uploaded. The next time I tried to synch something (5 seconds later) it got stuck. So I stopped the synch, unchecked the tracks and tried again. Now, no matter what, the moment I connect my ipod and try to synch it, it says synch complete. I'm pretty adept at Itunes. Everything is selected and deselected properly. These are not tracks I've downloaded, they're physical, actual discs (not burned discs). I've reset my ipod (holding the center and menu button) I've uploaded, unloaded, deleted, restarted, re-uploaded, checked, unchecked... everything I can possibly think of. I've tried to goole it and can find fairly similar situations, but how do you type just a few keywords into a search engine to explain all of this? Can anyone out there help me understand what may be going on? This is a HUGE pain. I really want to contact Apple about it, but I feel like I'm jumping through hoops of fire to find any decent contact information that doesn't include some fee for having my stuff fixed. I just want someone to talk this out with me. I'm fairly handy with a computer. If I can just get some additional troubleshooting options I may be able to work the problem out if it's easily fixable.

Answer 1

Good job explaining what has happened. That makes it much easier.
Although I am no expert, I surmise that by canceling the update, this left your library's data file "screwed up" for lack of a better phrase.
Here's what I would do:
1. Locate the location of your music on your system. It usually defaults to the C: drive under Music. Write down the file path if you need to, or remember where it is. If you don't know where it is, open Itunes, go to Edit > Preferences > Advanced and copy the file path that is in "Itunes Media folder location" field.
1.5. Go to File > Export Playlist and follow the prompts, if you can. PLEASE NOTE THAT YOU IF YOU CANNOT EXPORT YOUR PLAYLISTS, IF YOU CONTINUE THIS PROCESS YOU MAY NOT BE ABLE TO RETRIEVE THEM, AND WILL HAVE TO REBUILD THEM. (Also, note, you will not be deleting any songs or albums in your library, but the playlists are tied to the files discussed below).
2. Close Itunes.
3. Using explorer or by navigating into your C: drive either paste the file path that you copied earlier into the address bar or type it in if you wrote it down.
a. Within your library, (it may be up a directory or two, like in the one that starts with a folder "Automatically Add to Itunes") locate these files (use search as needed):
Itunes Library Extras
Itunes Library Genius
Itunes Library (the Itunes Database File)
Itunes Library (the XML file)
Itunes Music Library (XML file)
b. Select all these files by either control-clicking or shift-clicking.
c. Copy all the files by right clicking and selecting Copy.
d. Navigate to your desktop.
e. Create a new folder on your desktop by right clicking and selecting New, then Folder.
f. Name the folder Itunes Library Backup.
g. Open the folder.
h. Click once inside the empty folder and then right click and select Paste.
The above listed files should now be copied to the backup folder on your desktop.
4. Go back to your explorer page and reselect all the files above, and then delete them. (This is why you backed them up).
5. Uninstall Itunes.
6. Restart your computer.
7. Download and install the latest version of Itunes.
8. Launch Itunes. You're starting with a fresh copy of Itunes, so it will appear that you have no music. However if you keep your music in the default Itunes music location it will most likely add the music automatically.
9. If Itunes does not add any music, or asks to create a new library, tell it yes.
10. If you use a different location for the Itunes music library go to Edit > Preferences > Advanced and enter the file path of your library from earlier.
11. Finally, if you have no music in your library, in Itunes, go to File > Add Folder to Library, and then navigate to your library location. Depending on the size of your library it may take a few minutes to re-add everything.
12. Sync your Ipod.
I hope that helps. Let us know if you were successful in recreating your library.