Complete Movie Library Will Not Sync

I have an iPod Classic (160GB) and I am attempting to sync my iTunes library and all of the movies and tv shows will not sync to the device. Some of the movies sync. (approximately 80%). I have approximately 39GB of memory left so it does not appear to be a space issue. I have tried to restore the device without any success. Most of the movies that will not sync do have "iTunes Extras" and I have noticed that when I connect the iPod it does give me an extended "colored wheel" experience, i.e. it takes a long time to process.

Any help will be appreciated. Thank you.

iPod software version: 2.0.4

iTunes software version: 12.1.0.50