Ipod Nano & 2nd Generation Nano Problems

I bought an Ipod Nano last December and my brother recently purchased the 2nd generation nano.
With my nano, an ITunes CD came with it. I installed it and things worked great. However, my brother did not receive an Itunes CD, the instructions directed him to apple.com to download the latest version of Itunes.
We downloaded the latest version and every song that I had on my ipod (about 427 songs) showed up. About 5 of those songs showed up on his. (We connected his ipod through the USB cable that I got with mine).
Out of the 427 songs I have on my ipod, he wants about 25 and then the ability to add more songs that he wants onto his.
The question is how can we do this? When his ipod is connected all the songs are showing up on the itunes screen (and the 4 or 5 are showing up on his ipod screen). NOrmally in the version of Itunes that I used, once I made any adjustments to my itunes I could go to file and then "Update Ipod" and the changes would occur in a matter or seconds. In this case he has options like "Sync..." or "Transfer purchased..."
I don't want to lose all of the songs that I have due to this, so could anyone help us out?
Thanks in advance!

Do these songs play ok in iTunes?
Have you restored the iPod and reloaded the songs?
You should also try deleting them from iTunes altogether and re-importing them, then transfer to the iPod again.

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(82162)

TS1369 Hello! I have an Ipod Shuffle 2nd Generation and it is not recognized by my Windows 8 based laptop. An error message of 'USB device not recognized' is shown. I have the latest ITunes version installed, and tested the dock in other pc's.

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