Syncing with iTunes on Windows weirdness

Question

SO I have a 32G 2nd gen iPod Touch, which I sync with a Windows 7 PC.
And I've had this weird syncing problem for a while through. Through several versions of iTunes and firmwares for the iPod.
The problem is this. Every so often (every 3-6 syncs) after syncing my iPod, the iPod can not see any of the music on it. It would say 'library empty'. And the only way to force it to see my library again is to reconnect it to my pc and add some content to the iPod and it would resync the library. Its like sometimes the syncing would push a blank database to my iPod.
Anyone had such a problem? Know would it could be? To me it sounds like a problem with iTunes.

Answer 1

what you're experiencing MIGHT be due to your "iTunes Media Folder Location" setting, but I doubt it. the only similar situation I've had is when my iTunes Library is not detected because I forgot to connect an external drive. In this case iTunes resets the Location setting back to "My Music>iTunes>iTunes Music", which is (of course) empty.
it is possible to "rebuild" the library as you stated.
If you want to try to do this, first pick a time when you have a lot of free time to work on it, then follow the directions below:
1)close iTunes. make sure your iPod is not connected.
2)copy (backup) your existing iTunes database files somewhere safe (not in your iTunes folder).
3)delete the iTunes database files you are currently using.
4)open iTunes (and it will recreate new/blank database files for you to work with
5)make sure your iTunes Media Folder Location is correct in Preferences>Advanced.
6)deselect "keep iTunes folder organized" and "copy files to folder when adding to library"
7)open Windows Explorer and navigate to your "iTunes\iTunes Music" folder.
8)take your time with #9
9)carefully select your music/videos/etc. (sometimes album by album if you have problems), and drag the files (not folders) into your iTunes window. This should add the file information to your new/blank iTunes database without actually moving your files.
10)when you finish an album, double check your folder/file structure in Windows Explorer to see what is happening "behind-the-scenes" of iTunes.
11)if everything is correct, and you've finished adding everything to your new iTunes library database then start looking in iTunes to see how it organizes your files there. Double-check your song count/video count to make sure you have imported all your content, and that none of it is hiding unused in your iTunes Folder in windows explorer.
12)go back to preferences>advanced, and re-check those two check boxes (organize and copy files) once these are checked, iTunes will reorganize your files during the next few steps.
13)there is a good chance you will need to go through all your files to reassign some correct information (such as complilations, artist vs album artist info, etc.) (also your podcasts, music videos, etc. could now be labeled as movies, and need to be changed back to podcasts, music videos, etc.)
14)take your time in the "get info" window to make sure all your music/video/etc. information is correct.
15)It's a long, painful process, but you will be happier once it is completed. I have almost 400GB of media, and I've done this 5-10 times myself, so I understand any frustration you might feel.
16) once finished re-organizing everything, and you're sure it's how you want everything setup to sync, go ahead and connect your iPod and double check all your sync settings, then sync your iPod.
17)If for any reason, you want to go back to your previous database, just close iTunes, delete your current modified database files, and copy your original database files back to your iTunes folder in windows explorer.
18)If possible, I recommend you complete this whole process though, so that you will have a nice, newly organized database to work with, with all your media setup how you like it.
Let us know if this helps at all.
of course anyone else is free to suggest help as well.