Cannot sync certain music to my iPhone. HELP PLEASE

Recently I have been unable to sync music that I did not purchase from iTunes onto my iPhone, for example, mixtapes. The music is in my library, but when I play the song it is instantly skipped until the shuffle reaches a song that I have purchased in iTunes. When I sync my phone I keep getting stuck on that "Waiting for changes to be applied" screen too. I was hoping with the new iTunes update the other day that this problem would be fixed and it still is not. As a user of iTunes for god knows how long now, this is ridiculous, and after two weeks now I still can't believe that in this new update the problem was not fixed. Anyone else having this problem? Help would be much appreciated. Thanks.

So I have found a common denominator to this phenomenon. After having the same problem, I started to recopy my playlist of 500+ songs in groups of 10-20, 30+, 75+, and then over a 100+. Any music I have purchased from iTunes won't copy, but everything else did. Unsure if I made a playlist called "Purchased" at some point or this is an iTunes default, I also noticed it had some of the songs contained in my other playlist and was showing on my iPhone. Regardless of what I did such as dragging music from that playlist to the other and clearing songs from that playlist, I removed it altogether from the iPhone itself vs. doing through iTunes. After that, music copied fine to my playlist.
So, my theory is that iTunes is getting tripped up on purchased tracks already showing on the phone and all songs are showing grayed out/dotted circle because iTunes can't resolve the conflict with purchased tracks.
Hope this makes sense and is helpful.

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