IPod does not update purchased music properly

We have been having an ongoing problem with music that is purchased on ITunes. After downloading the music from the Itunes music store, we try to upload it to the Ipod. It does not upload and I end up having to completely reinstall both ITunes and Ipod software as well as do a complete restore to make it work again. I would like to avoid this. Does anyone have any suggestions? It is possible that I have two IDs floating around out there as a result of the reinstalls that make that make the Itunes music and the Ipod unable to sync with each other? That's only a thought and I don't know where I would check this..

Here are the reasons that some files in your iTunes library may not be sent to your iPod:
Software needs to be updated
Download the latest version of the iPod Updater and then update the iPod.
After the update is complete, download and install the latest version of iTunes.
iPod can't play the type of file
If you're not sure what file types iPod can play, click here.
Media file can't be found
Double-click the song in your library and show iTunes where it is.
Media file not authorized to play on your computer
Double-click the media file in your library and enter your account name and password.
Too many accounts
There is already content from five other iTunes Music Store accounts on the iPod.
The latest version of iTunes explains most of the reasons why some files aren't sent to the iPod. Get the latest version of iTunes here.
If you are getting no message explaining why specific content is not being sent to your iPod, you may need to reset warnings on your iPod.

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    m9268ll   Windows 2000  

    Not Charge
    - See:      
    iPod touch: Hardware troubleshooting
    iPhone and iPod touch: Charging the battery
    - Try another cable.
    - Try another charging source
    - Inspect the dock connector on the iPod for bent or missing contacts, foreign material, corroded contacts, broken, missing or cracked plastic.
    - Make an appointment at the Genius Bar of an Apple store.
    Apple Retail Store - Genius Bar                          

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