After this though nothing else would sync - exactly the same behaviour as before.
The track played successfully on both devices. I said yes to the update and the instant the update was complete my playlist (and local file) started downloading on both my Android devices. I was trying to follow the above steps and while doing so, Spotify Desktop announced that an update was available. I did manage to cause one track to be downloaded _once_ under very specific circumstances but I have not been able to reproduce: I've tried multiple attempts at deleting playlists and adding different combinations of local files and normal spotify tracks, then downloading these on two different android devices but without success. I tried those steps but it made no difference to me.