Yes, it is possible to play back a MIDI item on a track that has ReaInsert on it (configured to send out MIDI and receive audio). You'll have to set the track's input selection to "record: output -> audio (stereo)" and also check the option "Monitor track media when recording". I'd recommend that you set global recording mode to "time-selection auto-punch" and set the time-selection to be exactly the length of the item you want to record audio into prior to record the audio (this prevents the mess you might be getting with takes that have different lengths). You'll end up having a two-take item consisting of the original MIDI take and the audio take underneath.
I'm often doing this (without free item positioning). Keep in mind that you might have to disable some fx of the track's fx chain that don't make sense while playing back the audio take (like ReaInsert also). The same applies while playing back the MIDI take.
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