I can import music to itunes but cannot sycn to ipod

I can import files to itunes, but cannot sync to my ipod classic?

glutius
My problem exactly, for over a year.  I now have new songs on my updated iTunes but stilll have my old (but different) songs on my 2008 Classic iPod that I don't want to lose. 
I just read that the latest iTunes update may have solved this problem.  Is this true?!?  I've been dealing with this problem for such a long time now, I'm afraid of even trying to re-sync without more information.
Does anyone have the latest info on this?
Glutius, I'd like to know if/how you solved this issue and I wonder if anyone has found Wondershare or Emicsoft to be helpful?  Help

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