Unfortunately I can't seem to get this to work. What am I missing? Perhaps I am misunderstanding how this functionality is supposed to work, so I'm looking for some clarity/guidance. 

Did you enable the "MIDI over Bluetooth" setting on the H9?  In H9 Control if you click on the Pedal button in the bottom menubar and go to MIDI Settings, there's a "MIDI over Bluetooth" setting there.