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I do not see MachFive show up as a MIDI output after I pull it up on an audio track in DP 3
Make sure in FreeMIDI you have "Interapplication MIDI" checked under the File menu > FreeMIDI preferences.
Also, the audio or aux track MachFive is inserted on in DP 3 must have an input speficied. It doesn't matter what this input is, as MachFive will be triggered from by MIDI and not the input of the audio or aux track, so set the input to an unused pair or unused bus.