Music not syncing with iTunes 12.2

I installed iTunes 12.2 and signed up for the Apple Music trial. I have tried to sync my music both wirelessly over wifi as well as by plugging into iTunes on my Mac. I previously used a playlist to sync music to my iphone but now I cannot select just one playlist to sync. I tried copying the old playlist to a new one but some files are still not being not being synced (mostly mp3s downloaded from vinyl purchases, which is how I buy most of my music). Also, when I select the playlist on my iPhone I can't find a way to group the songs by artist which was my preferred method of organizing my music. So, the questions are as follows:

1. How can I sync just one playlist to my phone, including every song in the playlist and having all of them available for offline listening?

2. How can I group songs in playlists by artist and not have to wade through a list of every song (I have about 1500 songs in my playlist)?

3. How do I separate downloaded music that I own from Apple Music files available offline?

For what it's worth and if anyone at Apple is listening, it seems Apple has made playlist management between iTunes on the Mac and Apple Music on the iPhone needlessly complicated and unintuitive. Not only is this making me question Apple Music but it leads to concerns that I won't be able to play music that I own and have paid $$$$s for on my iPhone if I decide not to go with Apple Music over the longer term.