Why do some songs on iPod not appear in My Computer?

My iTunes library has most of the songs that are on my 60Gb iPod photo. It has approx. 2600 of the 2900 songs that are on my iPod. It is set to manually update as I don't want to lose the 300 odd songs that are on my iPod.When I open the iPod (E:) in My Computer, only the 2600 songs show though.Basically, there are about 300 songs that are on my iPod that are not picked up in iTunes library or My Computer.How do I get them into iTunes library so that I can finally set my iPod to automatically update?Please help.Thanks

Troubleshooting songs that skip
Try:
- Reset the iOS device. Nothing will be lost
Reset iOS device: Hold down the On/Off button and the Home button at the same time for at
least ten seconds, until the Apple logo appears.
- Unsync all music and resync
- Reset all settings      
Go to Settings > General > Reset and tap Reset All Settings.
All your preferences and settings are reset. Information (such as contacts and calendars) and media (such as songs and videos) aren’t affected.
- Restore from backup. See:                                 
iOS: How to back up                                                                
- Restore to factory settings/new iOS device.             
If necessary
You can redownload most iTunes purchases by:
  Downloading past purchases from the App Store, iBookstore, and iTunes Store

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    The information transmitted is intended only for the person or entity to
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