Apple Music / iTunes Library Issue

Ever since Apple Music and iCloud were introduced I have had issues with my iTunes Library. Things tend to disappear from my iPhone but still be on my MacBook. Music that I have uploaded from CD albums have issues as well for some reason. I tried Apple Music when it was released and then started to notice that the some songs that I have purchased or ripped from a CD in the past that I had dragged onto my phone through iTunes weren't play on my phone when I didn't have service. I looked at the file type by right clicking them and they were suddenly apple music files. I've tried waiting for my apple music subscription to end and then re-downloading those songs as the solution the genius at the Apple store gave me. I then tried apple music again and the same thing happens. When I sync my phone to my computer I receive an error like the one shown below.

Anyone know of a something else I could try or have been having the same issue?