Ipod won't sync certain songs after update to 5.1.1

I updated my ipod touch to version 5.1.1.  This included the addition of icloud to my system.  Since I have updated it, my ipod won't add certain songs from my itunes.  It's really weird how it just randomly selected songs to download.  I have songs in itunes that I purchased, as well as songs I imported from CD's.  Every song shows up on my ipod song list, however most are "gray" and won't allow me to select them to play.  (like they are not downloaded or something).  I have retored my ipod three times to see if that will allow all the songs to play on my ipod and it won't work.  Everytime I try to sync my ipod the fist song that tries to sync says "The file wasn't synced to the ipod because it cannot be read or written"......I have tried removing multiple songs and still get this message for every song. I did figure out that you can open the itunes store through the ipod and select "purchased".  You can then view songs that "aren't on the ipod" and manually download each individual song to the ipod, however, not only is this a pain in the *** and going to take forever since I have 1000+ songs and tv shows, but this still won't get all my own music added from CD's to my ipod. HELP! Any tips or solutions!! ( Also, I am a Mac user if that makes a difference)    

After over TWO HOURS on the phone with apple support I still had no solution.  There were several songs that would freeze up my itunes, then I got the message "blah blah song" couldn't be transfered to the ipod because the file was unable to be read or written.  The tech and I came up with the solution to just delete every song that came up on. In the end, I had to individually add EVERY SINGLE SONG to my ipod one at a time.  If an error popped up I just deleted that song and made a note of it.  I had no issues with the songs I imported from CD's, only the songs purchased off itunes.  The tech never could figure out why.  We rebooted, wiped clean, reset, anything...you name it we tried.  We even moved everything to another computer to see if it was a computer issue, then we wiped my husband's ipod touch to see if it was a hardware issue on my ipod. NOTHING. This finally worked even though it took all day.  Everything seems okay now, we will see the next time I add songs.  I did lose ALL my photos and videos taken with the ipod. :/ That really ***** because I have a 1 year old who's entire first year was on that stupid thing.  What a waste of a day.

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