I don't have a huge music collection from iTunes, but most of the few songs/albums I have are not showing up in Apple Music on my phone. I go to iTunes, and tap on the download "cloud" icon, it changes to "downloaded", but then reverts back to the download icon, instead of the "play" icon, and it doesn't appear in "My Music". I am on a family sharing plan, as well as a new iPhone 6s. It seems like I can download music from my family's account, but not my own, for the most part.