This is actually easy. For each source you want to send the monitor output to a second place, right click on the source and add the Audio Monitor filter, and then select where you want to send it.Audio/Advanced/Monitoring Device only has an option for one output. Is there any way to send it to 2 different audio devices?
This is a major simplification of the overly-complicated question I posted an hour or two ago (would delete it if I could).