IPod, iTunes won't work with each other

I have spent the last 2 days trying to update my "new" nano. The first few times I synced it up no problem. Now that I've spent a small fortune on new music, the nano and iTunes won't work together at all.
First, I have the most up-to-date version of iTunes. Next, I had the software update 1.1.3 for the nano all ready to go when I plugged it in. I hit the install new software button and dear god, if the nano didn't crap out and iTunes lost it and gave me a 1436 error. I had to disconnect the nano and reconnect. I tried several times, but finally gave up on updating the software.
I went on to try to sync the nano and iTunes so I could at least listen to my music at work, but iTunes now says I'm not authorized to play ANY of my purchased music (recently purchased or stuff I've had on there for years) on my computer so it won't copy it onto my nano. So I deauthorize and reauthorize my computer several times, I've read every possible troubleshooting/solution guide I can find on the site and NOTHING works. I can play all my purchased music in iTunes once I've reauthorized my computer, but as soon as I plug my nano in - forget about it - "You are not authorized to play this music on this computer" crap. And I can't even restore the nano b/c I get that stupid 1436 error - and believe me I tried everything those help pages suggest.
I'm at a loss here and not in the least bit happy with this thing.

Problem solved. The harddisk was formatted and Windows and iTunes re-installed. Hopefully this problem won't appear very soon.

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I searched the whole web, but nowhere getting the answer.
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All personal links to PC-Doctor software removed 8/2012 by mfg request

IPod, iTunes won't work with each other

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