Purchased Music on iPod will not play in iTunes

I'm trying Authorize my work computer to play my purchased iTunes songs from my iPod, No Luck. It's just keeps asking to authorize, I authorize then it say it was successful.
Try to play and it asks me again...again...again.
I'm running Mac OS X 10.3.9 on a DUAL 1GHz PowerPC G4
iTunes 7.1.1
Thanks for the help
-Rick
iMac G4

I tried all of these steps, but I'm still not getting the Ipod updater to even recognize that my Ipod is plugged in.
The computer is recognizing that the Ipod is plugged in, and it opens Itunes 5.0 like usual, but after I connected my Ipod to sync for the first time since installing 5.0 it erased like 200 songs off my ipod, and says that
"Some of the songs in the Itunes music library were not copied to the Ipod "My Ipod" because your Ipod software is too old. Go to www.apple.com/ipod to get the latest IPod software update."
every time i try to get those songs back on. I believe the songs it erased are ones I purchased from the Music store.
Recap:
1. Ipod is being recognized and can be seen in Itunes.
2. Itunes says my ipod software is too old to load some songs from my library.
3. Ipod updater 2005 9_06 will not recognize that my ipod is connected to my computer even though it shows up perfectly on my desktop and in Itunes.
4. My ipod itself is running just fine, its just missing like 100$ worth of music i purchased : (

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Purchased Music on iPod will not play in iTunes

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