Struggling with iTunes Sync

I'm really struggling with how iTunes sync is supposed to behave.

Ideally, the changes that I make to playlists in iTunes would automatically update in Rekordbox when I synced appropriately. This would include:

1. Order of songs in playlists

2. New songs imported to collection and added to playlist

3. Songs removed from playlists removed in Rekordbox.

I can't figure out how to make any of this happen. Whether I refresh the iTunes library in the Playlist panel or use the Sync function that I use to then also sync from Rekordbox to USB, this isn't what happens.

Instead what I need to do is reimport the playlist from the iTunes section into the Rekordbox collection. Problem is...when I then go to export that playlist to USB again, it removes all of the songs and then re-exports the entire playlist all over. This isn't good for the health of the USB device long term.

I'm hoping there's something that I'm doing seriously wrong. Any suggestions?