1 computer, 3 Mac OS user accounts, iTunes account for each Mac OS user, authorization problems

We have 4 computers for 3 people in our household: 1 iMac (recently purchased), 1 MacBook Pro, and 2 MacBooks. We were previously running off of just the MacBooks (1 for each person), but we decided to buy the iMac and use it as a hub for all of our pictures, music, movies, etc. We were sold on this idea after learning about the "Automatic Downloads" feature, where all content would 'just sync'. We each have a separate Mac OS user account on the iMac, with our own separate content libraries. We each have a separate iTunes/AppStore account. It seems like a good idea until...
When I tried to turn on Automatic Downloads in iTunes on my iMac, I got this message: "You can auto-download purchases on this computer with just one Apple ID every 90 days. You cannot associate this computer with a different Apple ID for 87 days". I tried to turn on Automatic Downloads on my MacBook Pro, when I got this message: "You can auto-download purchases on this computer with just one Apple ID every 90 days. You cannot associate this computer with a different Apple ID for 90 days". I did not necessarily want to download the apps/music/books to this computer anyways, as the reason we bought the iMac was to serve as a hub for all of this content, but it was still frustrating to see that message.
I have tried everything suggested on the authorization troubleshooting pages and forums (e.g., authorizing, de-authorizing and de-athourizing all, and reauthorizing), but I have not had any success. I have contacted Apple several times, but I get tips on how to ensure that I have the most up-to-date version of iTunes on my computer, or how to manually download pre-purchased content. I will not begin to explain how frustrating these low-level responses are when the issue is much larger.
I have a few theories of why this is happening, one of which is that we will only be able to authorize one of the users iTunes accounts to this iMac (despite the fact that we are using separate Mac OS user accounts). This may be the case if iTunes authorization identifies or registers the computer based on its serial number (or some other unique identifier), rather than the Mac OS user account. If that is the case, then I suspect that purchasing this iMac as an automatic download hub for 3 separate Mac OS users was pointless, and I will gleefully warn anyone away from trying to do that.
So my question(s) read(s): How does iTunes account authorization identify/register with the computer? Is it authorized to the computer serial number, or could it be authorized to a Mac OS user account?
However, if my above theory is true, then my question is: Do I have any other options?
Thanks!

I just had this problem because I logged into a friend's account on the computer I'm on now, and used the Previous Purchases feature. Well, that in turn deactived my use of the iCloud and iTunes Match on this computer when I signed back into my personal iTunes account. iTunes Support was no help, they just gave me a scripted response I would find online myself. Tried many different things, but what actually worked, was changing the Computer Name on this computer, and rebooting. Now, iTunes recoginzes this computer as a new device, yet, still is one of the 2 authorized computers on my iTunes account. Try changing the Computer Name on your troubled machine, then try associating it once again, see how that works out for you.

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