18.5GB ipod wont play any song Ive bought on iTunes after two days

I don't know what generation it is, but it says version 3.1.1 and model number M9282LL in the 'About' section
I have to plug my iPod into my machine every two days or it will start skipping through any song I've ever purchased on iTunes. The only songs that will play after that are what I've ripped from CDs. Even when there is nothing to update, I must plug the iPod in and let it run through the update routine. It then works fine for another 2 days. I've searched here and found nothing. Nobody Ive talked to in the mac stores have ever heard of this happening. Any ideas?
TIA

Once you have made sure that both the iTunes and iPod software are current and have deauthorized and reauthorized your computer, if the problem still exists, try this test:
1. Deauthorize the computer.
2. Create a new user in the system.
3. Download the free song of the week from the iTMS in the new user account.
4. Play the song in that user account to authorize again.
5. Restore the iPod (using the iPod updater) in the new user account.
6. Sync just the free song of the week and see if it plays on the iPod.
If it does, you appear to have a corrupted iTunes library file, and you should recreate the iTunes library file in your normal user account, and then sync your music back to the iPod and all should be well.
The following articles will help you.
Authorization and Deauthorization.
How to create a new user account on a Mac.
How to restore the iPod.
How to recreate your iTunes library.
Apple are also working on the theory that this may have a connection with the iPod entering deep sleep and not playing purchased music afterward until you resync it again.

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No sound through stereo headset1
Inspect the headset jack for debris and clean if necessary.
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http://support.apple.com/kb/TS2802
Take care, and thanks for visiting the Apple Support Communities.
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18.5GB ipod wont play any song Ive bought on iTunes after two days

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