Repetitive authorization request; Sync Problems

Hello,
Lately, I've been using iTunes (PC) to listen to my music on iPod, because I don't want to overheat my external GB hard drive. I don't have to turn on my HD; I just plug my iPod via USB. I often burn new music onto my HD and then sync to my iPod without any problems until...
Yesterday, I decided to plug my iPod into an iMac and chill. My iPod was set on "manual management"; and the iMac did not ask to authorize the use of my iPod on its iTunes... and so I played music off my iPod.
A few hours later, I go back to my PC; burn some music; and tried to sync my PC iTunes (HD) to my iPod... and I get this repeating dialog box asking me to authorize this computer for the 400+ purchased songs.
Now, I did what iTunes support pages suggested: 1.) Authorize computer via administrative account... except, I don't think authorization via administrative account applies to Windows limited account. 2.) I deleted the SC folder.
Then nothing syncs.
P.S.
Oh, I see... I forgot to set my preference and connect to my external HD.
Now it syncs.
But my question is: Why does it seem that after I use my iPod thru iMac iTunes that I start to have problems with Windows and the repetitive authorization request? ... Is that a bug?

see above

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