[SOLVED] Repairing iTunes?

Uninstall, Revo uninstaller, long check HD SMART status, reinstall iTunes.
Test on another computer running the same version of Windows. If fine, then look to reinstall Windows on the customer's computer.
 
Repairing and then reinstalling iTunes didn't work on the old computer. iTunes Package installer told me the installer was corrupt. I even downloaded twice.

Moving on.

Each person has their own Brand New Laptop, so I transferred the iTunes Library for each user into the appropriate computer, after downloading iTunes.

One computer's iTunes Account can only access half of their content.
"iTunes repeatedly prompts to authorize computer to play iTunes Store purchases"

I have authorized their account and their sister's account, but nothing actually authorizes the account even though iTunes says it has authorized.

I believe the purchases that don't play are tied to their sister's account.
All purchases are playable on his iPod, so I know it did work before iTunes broke.

I'm looking online for solutions but their are 101 things that might fix this problem. I've already spent hours trying to get iTunes to work correctly.
What do people recommend?

I didn't see anywhere that the libraries on the old machine were de-authorized. If they have more than 5 authorized devices, there is going to be problems. So, if you or they keep on authorizing devices without de-authorizing iTunes will throw up flags.
 
Currently using a new laptop with new iTunes.
iTunes tell me only 2 - 3 Authorizations each.
Yes their are only 2 Accounts and both are activated under the new laptop.
But half the music tells me to authorize again and again, even though it has told me it has been authorized.
 
Currently using a new laptop with new iTunes.
iTunes tell me only 2 - 3 Authorizations each.
Yes their are only 2 Accounts and both are activated under the new laptop.
But half the music tells me to authorize again and again, even though it has told me it has been authorized.

Some of the media might have been purchased after the device was authorized a second or third time so it's not tied to a bunch of devices like the problem media is. Or else....it's illegal pirated stuff, simple as that.

It's obviously a DRM issue. I'd try de-authorizing all of their machines to really see if it's a DRM issue and go from there. I can't see how it wouldn't solve the problem if it's legit content.
 
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Thank You Anonymous Mac Tech.

Deactivating all itunes machines solved the DRM problem.

Some of the media might have been purchased after the device was authorized a second or third time so it's not tied to a bunch of devices like the problem media is. Or else....it's illegal pirated stuff, simple as that.

It's obviously a DRM issue. I'd try de-authorizing all of their machines to really see if it's a DRM issue and go from there. I can't see how it wouldn't solve the problem if it's legit content.
 
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