How about if I send a MIDI Command from my Helix via the H9 to the iPad?

Will that be a reliable connection? What do you think?

Well Helix is the same as H9, which doesn't support Bluetooth MIDI.

You'll need something like these to work with your Helix.

https://www.cme-pro.com/widi-jack/

https://www.sweetwater.com/store/detail/MDBT01–yamaha-md-bt01-bluetooth-wireless-midi-interface