http://www.apple.com/feedback/
Are all of your files in AAC format? If you have any MP3's, add them to your library in Windows Media player and test them. Does each song skip in all of the same places, or is the skipping different each time you play the same song? If the skipping is inconsistent within the same, song, I'd suggest reinstalling iTunes and QuickTime:
Go into Control Panel > Add/Remove Programs
Remove these applications:
1. Apple Software Update
2. Apple Mobile Device Support
3. iPod for Windows (this may or may not exist, either way, it's not needed so we can remove it)
4. iTunes
5. QuickTime
Restart the computer
Download & Install the Windows Installer Cleanup Utility:
http://support.microsoft.com/kb/290301/
Launch the Utility: Start > Programs > Windows Install Clean Up
Select any of the above mentioned applications, and click Remove
Restart the computer again
Download & install iTunes again from here:
http://www.apple.com/itunes/download/
If the song skipping is consistent each time you play the same song, it could well be an issue with the files. Do you have a backup that you can restore files from? If you do, try that.
CG