It’s very strange the way MIDI Insert recording is handled… it forces you to enable disabled inserts in order to record the last insert:
I’m tagging this as an issue because it seems to strange
my suggestion is that there is a record-all/carry-through record button next to the bypass button on the MIDI Inserts tab:
There should be a bindable shortcut key for this so that multiple tracks can all have their MIDI inserts record activated at once.
edit
on a side note, there is sometimes some very strange behaviours when activating MIDI record during playback I think. tempo sync goes weird or maybe parameters change sometimes, random notes played. intermittent random weirdness.