ITunes says it needs to upgrade but the download never works. What's wrong?

One day I got on iTunes to put some music on my iPod Nano (one of the older versions), and always before when I plugged it in and came up and said it was plugged in, but then it didn't recognize it! This went on for several months, me never being able to put more music on my iPod.
Finally I got the newest Nano for my birthday and I figured it'd work, but the same problem is going on! I've had the brand new iPod for 3 months and it doesn't have ANY music on it!
It does come up and ask if I want to download a newer version of iTunes, that it needs that one to work right (version 8.2 something I think). I go to download it, it takes a while, and then comes up and says the download was unsuccessful, I've tried about 30 times, and it never works.
What is going on?

Instead of trying to update iTunes +from within iTunes+, go to Apple's page where you can download the iTunes 8.2.1 installation file -- save the file, don't run it direct from the download. Once downloaded to your computer, then run the installation file.
If that does not fix the problem, then remove the following software from your computer (you won't lose your music): iTunes, Quicktime, and something called "Apple Mobile Device Services". Once you remove those programs, then run the iTunes installer file (from above) again. That will install all three of these programs and should fix your problem.

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