Some of my Playlists on iTunes will load to Apple Music, others will not ...

Some of my iTunes Playlists loaded into Apple Music but others have not. I assume it is because some of the items in the Playlist will not load into the iCloud (e.g. videos, digital booklets, etc.). In earlier versions, I was able to look for an icon to tell me which item was not "uploadable." I can't find that now. How do I identify items in a playlist that are causing it to not upload to iCloud? Once identified, if it is a song, how do I re-download from Apple Music without having to buy it again?