Uploading problem/question

ive added music to a few of my friends ipods. One of them has the Nano, the other has a 60GB iPod video. Uploading music to the 60GB was as easy as plugging it in, and dragging music onto the ipod icon on the left playlist screen in iTunes. With the Nano, not so easy. It doesnt allow me to drag anything into the iPod icon while its connected, and when you actually click the icon to see whats on the iPod, all of the songs are dimmed gray. Where as the 60GB's songs were normal, and black in color. My 30GB does the same thing as the Nano.
I've tried to make a playlist of the specific songs i want uploaded onto the Nano, and ive made it so it updates only that specific playlist. But when i do, it overwrites all of the music previously on the Nano.
Is there anyway to make it so the songs arent dimmed gray, and i can just drag songs to the iPod icon to be uploaded? Or is this just some special feature that only the 60GB has?
If anyone could help, it would be GREATLY appreciated.
Compaq   Windows XP  

music downloaded from websites such as Purevolume.com, myspace.com, and other mp3 hosting sites where the band allows you to download songs. The two people ive helped out are either computer illiterate, or they dont have easy access to the internet.
even if i were to put a cd that i purchased onto their ipod (which im not). That is about as harmless as walking across the street outside of a crosswalk. Its illegal, but who really cares. Once its on their ipod, they wont be sharing it with anyone, and i have better things to do other than adding music to every one of my friends iPods. Its just these 2, thats all.
My question was just wondering why, on the Nano and 30GB, the music, when you click on the ipod icon, is dimmed gray, but on the 60GB its not. And is there a way to change this.

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    Because this process creates an entirely new library and leaves your old one untouched, it is non-destructive, and if you're not happy with the results you can simply return to your old one.  
    Reverting means restoring your Librry from Time Machine and re-installing 08. It's not a big thing to do.
    Contact App Store support about a refund. There's an email link on the right hand side of the app store window.

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