So continuing on the same save file and before activating "Enable Debug Trace"...I found that 1/2 of the Detroit Red Wings didn't have face gen.
Regenerating the faces didn't work until I exited the game completely, reloaded the save, and now regenerating works.
Since I am aware of the Enable debug trace feature now, I will do my best to recreate the bug and send the .txt whenever it occurs immediately.
In there meantime, here is what the trace looks like at the moment.
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