Why can Itunes not read my ipod's content?

Everytime I do an update on itunes it works perfectly fine.  The second time I open up itunes on the most recent version it says it cannot read my ipod's conent.  So it's not my ipod that doesn't work since it can work the first time it is on itunes, it is itunes that does not work.  I don't have a backup file for my songs and I do not want to restore my content.  I just want to add more music from itunes which does work THE FIRST TIME.  The last time I even tried to restore my ipod to factory settings it wouldn't even let me.  It also isn't letting me doing any updates on my ipod for some reason and it says I'm still on 4.3.5, but that isn't even an option below.  (I hate itunes, it's far too complicated than it really needs to be).

Okay, so I had persomed a diagnostic check, and it said ipod not found.  Does that help or make it worse?

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