My music workflow is the following: I’m using dynamic playlists based on last played timestamp. If a song was played, it gets a new timestamp and is removed from the playlist. Now a new song comes automatically in to the playlist where the timestamp doesn’t exist or is older as x-days. That’s easy to setup on strawberry and other applications. This playlist will be synced via whatever you want to your phone. In my case a SFTP service to keep it wireless. On the phone I use the same playlist with every player you want. Additional I’m using lastfm to scrobble the played music. This keeps the last played timestamp on the phone and can be synced with strawberry. I don’t know if other applicants can do the same.
Sounds complicated at first but after initial setup it’s a automatic process.