New to this iPOD game, and having problems! Please help!

So I finally got my hands on a Nano yesterday, and ever since then some odd things have been happening. I would appreciate any help to the following questions/problems I've been having, because the applecare stuff does not seem to really be either helping or addressing my issues.
1. When starting iTunes, I was told (once it reconized my nano) that I neeed to install the new software for the nano, i expected this and downloaded it, and followed the directions. As soon as I did that though I started getting "Corrupted Error" messages in iTunes. To get this to stop I just reinstalled iTunes...I was able to transfer things now, but now the system does not seem to reconize that the nano has the new software, and asks if I want to install it, and when I do...(again) I start getting those corrupt errors again.
2. I will move some songs from my iTunes library, to my nano, and it says they transfer over. I then eject my nano from iTunes, wait for the "do not disconnect" to go away, and unplug it, and sometimes, my newly transfered songs are no longer on my nano. Am I doing something wrong?
3. I went to update my iPod with some playlists from my library, I went to the options, and said "only update from these lists" It updated my ipod...and deleted everything else off of it, and to add insult to injury, it only added the title of the play list, and NOT the actual song files
I know this is a lot, but I'm really frustrated, so any help would be appreciated.
Thank you so much for your time.

Hi,
Read this link if it happens again: iPod: What to do if Windows displays an "itunes.exe - Corrupt File" message
There is another post I think it is in the User Tips Library that goes into more detail as well.
Regards
Colin R.

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