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?