Purchased songs from Itunes STILL not playing on ipod mini

I read all the posts about this issue, of purchased Itunes songs not playing on ipod. I deauthorized the computer and all computers associated with the account. then re authorized them. I reset the ipod several times, and also restored the ipod. I reinstalled the itunes software. I changed the sync to manual. removed one of the purchased songs. reauthorized the computer, then manually added the song back. I renamed the song. I even tried with downloading the free song. Any other suggestions. It made me look bad when after all of this I still could not fix the users issue. Other than declaring it a HARDWARE issue, I thought there could be a registry setting with the authorizing that did not happen properly. Has anyone else experienced this issue , and NOT been able to fix it. It would really appreciate any advice. My only conclusion was hardware, and the user states they had already spoke with apple who declined to help.

It may be an authorization issue. Both iTunes and the iPod need to be up-to-date.
Usually, you need to play at least a part of songs purchased from the iTMS within iTunes to authorize them. They won't copy to your iPod until you do this.
How to transfer Purchased Music from iTunes to your iPod
iTMS Song and Computer Authorization
If you've played & authorized them in iTunes and they still skip, try this. De-authorize the computer in iTunes/Advanced menu, then re-authorize it. You re-authorize it by playing one of the songs purchased from the iTunes Music Store within iTunes. It should ask you for your Apple ID and password, and then the computer will be authorized again. Sync your iPod with iTunes, and those songs should play on the iPod once again.
Another common cause of this is not having the latest version of iTunes.
If you are using the latest version of iTunes (6.0.4), then you need to make sure your iPod software is up to date also. Get the iPod Updater software, install it, run it and update your iPod.
When you have done this, authorize your music in iTunes by playing a few seconds of it within iTunes, re-sync your iPod, and it should transfer by whatever synching method you choose.
If the above 'standard' fixes did not help, then it's a bigger problem that I can diagnose...

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    Click on the link to see more details and screenshots.
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