iTunes and 5th Gen iPod?

camgangrel21

Mac Programer
I just won a 5th Gen iPod the other day.
I got it setup and working I have all my tracks on it, now here is what has gone ape.

I had a 2nd Gen iPod mini that worked just fine till it's hard drive went south.
Now when it worked I could click on it in the iTunes list and take and click the eye in the upper right hand corner of iTunes so I could say just find all of just one artist songs.
Now I have my 5th Gen setup the same way I had the mini but when I click on it the eye in iTunes is grayed out and so it the song list.
How do I go about making iTunes let me say take 2 or 3 things off my iPod with out having to let it reload all of my stuff?
Any help on this and I will jump for joy.

Thank you all for your time,
Michael

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I can also be found at The Cam Report. Taking a look at all most everything Apple.
 
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