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While this is really nice, I'm now realizing the plugin on the MIDI output bus can't be automated. At least not without using a mapped controller which just begs to be forgotten about and/or overlooked given time.

The compromise would seem to be to abandon the splitting of the MIDI tracks and just consolidate everything to a single track. That way, the plugin would be associated with the track itself which means it would be reachable via automation. The single track would still use the multi-out audio bus which routes down on a per channel basis (via inserts) in order to isolate things for additional processing.