IPod not highlighted in iTunes for content editing

I've got a Mac G4 using an OSX version 10.2.8 operating system. I just got a Nano iPod and am unable to transfer files to it. I've downloaded the most current available iPod drive and updates but after plugging it in, the iPod icon appears momentarily on my desktop and then disappears as my iTunes window opens. The iPod and its contents are visible as an option in iTunes but not highlighted for editing--what's the deal, Neill?

The songs are "greyed out" because you have the iPod set to transfer songs automatically. If you want the songs to be bold and selectable/editable, then you need to change to manually managing your songs.
Please not that by editing/changing the songs on your iPod in this manner, the changes will not affect the songs in iTunes, only on your iPod.

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