Bumping this old thread to ask: I’ve discovered the downside to using a second Monitor out for your headphones in Control Room as opposed to using a the Add Headphone option, and it seems like you can’t have both outputs active simultaneously. Am I wrong about that?
In my case I wanted to hear both click and MediaBay preview in my headphones so I created a second Monitor bus and set the outs to my headphone hardware outs. Seems to be working fine aside from needing to manually switch outputs in CR, which is not ideal in my setup.