I set up a call with Apple Support to talk to a live person.
It was a terrible experience but I got it fixed.
Set it up to call me at a specific time.
First call - After explaining about 5 times and transfered the same amount of times, the final person I talked to got very combative and hung up.
Setup another call back and being transfered around 3-4 times, I got to Audrey, who I was told was a "Senior Advisor". All I can say is... it's the support employee I wish I got first. She wasn't with the iTunes team, but chatted them, tried some stuff.
Finally it came down to that there was "another ID" attached to my mac. I have multiple User Accounts on my mac, but they said it shouldn't matter. I had never used another account within iTunes (though my iCloud account is separate, it has never been used in iTunes).
She said they removed that account, and told me to wait 15 minutes. She setup a callback. I waited 15 minutes, and it worked.
Audrey called me back, gave me her email address and callback number in case further issues come up with this.
The first 7-8 people I talked to made me feel like I was calling just about every other support line (and I expect more from Apple), but Audrey, singlehandedly, restored my faith that support means helping the customer (and not simply saying they are sorry over and over without doing a thing).