Will not update itunes

I added more music to my i tunes and it exceeded the space left on my i pod mini. So I chose the option to have a random i pod "selection". Then I went to update it and it deleted the play lists I created so I went back to my library and unchecked some songs so I could have all the ones I wanted to fit in my library on my i pod and deleted the "i pod selection play list". Then I got a pop-up saying "cannot be updated because selected play list is missing". So I went back and added the i pod selection play list and copied my music from my library into it and it still will not update my i pod!
HELPPP PLEASEEEEEEEE!

I wish I had an answer for you, but what I do have is the same problem! Suddenly, even with the latest iTunes software and iPod updater, I can no longer update from iTunes on my 3rd generation iPod! After that, audio no longer works on my system. If I do a restart, it still doesn't work. The only way to get audio back is to do a cold boot. But then, even after that, the iPod problem remains. I wonder what's going on here.

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