Multiple Issues with iPod Classic 160GB

In mid-November 2009 I bought a new 160GB classic. I connected it to my Windows Vista PC and immediately got an error saying that the computer was not authorized (note that I had been syncing an 80GB Classic and three Nanos fine before this). And despite logging in with my valid iTunes account, it would loop endlessly, telling me the computer was already authorized, then prompting me again.
I posted a forum question on November 18, to which I got three replies, all of them with them same problem (and no solution). I tried all of the things suggested in Apple's support entry: my one workaround is to run iTunes as Administrator every single time I launch it. Still get the annoying authorization message every single time, but it at least syncs.
BTW, I now need to go through the same ludicrous procedure every time I want to sync one of my other iPods.
But wait! There's more!
There is a firmware update for the 160GB Classic (2.0.4), as well as for one of the newer Nanos. Each time I try to install, it fails with Error 1436. Apple's suggestion to try restoring the iPods similarly fails, as does every other "fix.".
I have tried everything on Apple's official support site, including reinstalling the Windows USB drivers, Apple Mobile drivers, re-registering DLLs etc. Plus I even uninstalled/reinstalled iTunes.
Considering the $700 or so I have invested in Apple iPods, I am getting mighty irked. Fortunately, I have a smaller investment in iTunes purchases and do not plan any future ones unless I can feel comfortable that these problems are solved.
Is there any solution to these problems?
Windows Vista SP2
iTunes 9.0.2.25
Patience (downgraded to 0.4.1)

You cannot copy media from one iPod to another directly. The content on the one iPod must be stored in your iTunes library on a PC or Mac before it can be synced to the new iPod.
See this excellent user tip from another forum member turingtest2 outlining the different methods and software available to help you copy content from your iPod back to your PC and into iTunes.
Recovering your iTunes library from your iPod or iOS device
B-rock

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