IPod touch 5 won't sync without restore

for the past few months my iMac has not been syncing music to my iPod. Whenever I choose to sync my iPod it goes through the process and shows 'step 1 of 7' and then will jump to 'step 4 of 4', with 'waiting for changes to be applied'. after the sync has finished, no new music has been added to my iPod. if i choose to sync again, the sync doesn't stop. even if i choose ti cancel, the syncing icon will still appear in the corner of my iPod screen. even after i have ejected it. After this any music that has not been purchased through iTunes no longer appears on my iPod.  i end up with a large amount of memory in the 'other' section, which is equal to the amount of memory that would have been taken up if the music had synced, but there is no music on the device,. I have tried manually syncing my iPod and syncing using the wi-fi but nothing ever works. i always end up having to restore my iPod and set it up as a new device. if i restore from a back-up, the iPod does not sync at all and the large amount of 'other' is still there. after i restore i can sync my entire music library once and after an hour/ 2 hours my sync will be finished.
I'm currently running iOS 8.1.2 on my iPod and i have yet to update to os x Yosemite as i have read stories about libraries being wiped. i do not want to risk the update until i have backed up my music and several thousand photos onto external hard rives as i do not want to risk losing any of my photos. As i've been writing this post, my iPod sync has been frozen on 'waiting for changes to apply' with the large amount of 'other' taking up all the memory.

Re: What does the gray dotted circle in iTunes mean?
what does the dotted circle mean?
https://discussions.apple.com/message/20813679#20813679

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