Purchased music on Macbook Pro does not agree with the purchased music on iPad.

I have current versions of all software. And just bought a new iPad. When examining purchased music in iTunes on my MacBook Pro, it is pointing to current purchases over the past few years. But when examining purchases in iTunes on new iPad, it is pointing to very old purchases made several years ago. The purchases to do not agree - they are not in sync. I want them both to be in sync, or at least have both devices point to the current purchase list. Thanks in advance.

I have my iPhone attached via USB cable to my MacBook Pro.
I have been able to successfully sync my calendar now by activating iCloud on my iPhone and via System Preferences on my MacBook Pro after I learned that Maverick does not provide iSync.
However, I have a new problem: The calendar does not "upgrade" (it gets stuck) and I receive a "403" error and it gets stuck in a loop that I have to force quit. I have looked that up in the forum, but wasn't able to solve this issue because the solutions are way to technical and out of my league.
Very disappointed development as removing calendar from iCloud now also deletes all my entries on the Mac.

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