I have the same experience with my setup, I can't seem to get the Developer mode option on the watch.. Tried everything above too, nothing.. then I moved to a remote work location on a different WIFI network, opened my xcode and VOILA, everything started working! I do need to investigate some more, but this could maybe related to wifi policies, like broadcast-to-unicast conversion or blocked traffic... I did not get it to work on Ubiquiti, it works like clockwork on a Cisco wifi.. not sure it's vendor related, but I do believe Wifi settings are impacting connectivity.