Here's what happened: I bought a new iPad. I was setting it up, and, as I remember it, asked for my Apple ID and I flubbed it. I think I said 'Skip' and it asked if I wanted to enable email, and I said yes. It then asked for an email address and I entered my iCloud email address and it complained that it already exists. Yeah, no duh... But it wouldn't let me go on without entering 'an email address', so I entered my work email address, and it went merrily along it's way, and somehow all of the iTunes stuff I had up to that point was assigned this new Apple ID.
At the time, I didn't realize that I was actually creating a new Apple ID. Not until it was done. Which was odd, because my, at that moment, 'old' email address came up fine on the new iPad, and everything continued to work, play, be readable. I didn't at the time realize that I had created a schism that would overturn damn near everything that I thought was reality about 3 years later.
I thought that all of my iTunes content was under the first account, but it had apparently been 'transferred' somehow to the new account.
So there I am standing there telling someone at the Genius Bar that I want to kill the account that they can see has everything I own from Apple as far as content goes killed. After they explained it to me, I understood their bizarre looks when I was trying to explain what I wanted...
Nothing, from the Apple/iTunes standpoint was anything close to what I thought it was. I was dumbstruck.
That one mistake threw everything in disarray...
And when they finally explained this to me, I asked them then why all of my existing iTunes content was assigned to my 'new account', and why they couldn't just 'unassign' it from that one, and put it on the one I swore up to that day was the 'real account'.
I walked out more convinced than ever before that iTunes was a screwed up mess... I mean, hell, search the forums here and on the Apple support blogs and you will find all of the times I've blown up parts of the iTunes database on my iMacs...
But anyway, to your point: Yes, I'm stupid. I did this all myself... I like pain...


I counter that it was far too easy for this to happen, and obviously Apple didn't plan for it.
And I still wonder, to this day, how, if they can't transfer purchases, how all of mine got 'transferred' to my new account.