Re-Syncing Same Playlist Questions

[MPG]

I have a running playlist that I manage (not auto-playlist). I'm continually adding and removing songs depending on my mood. I'm curious about when I sync it to my phone (Samsung Galaxy S7) from MMW (latest version). Does MMW transfer files that are already on my phone or does it skip them? Does it matter if the song order changes? Do I have to delete the songs off my phone? Playlist only has between 400 and 500 songs.

I'm asking because quite often I get the dreaded, long time to sync error.

[Lowlander]

MediaMonkey should only sync those files that are not on the device yet when using Auto-Sync (wifi or USB), not re-sync files already on the device.