Any chance that this is possible?
Bluetooth audio redirection. Instead of having the audio go to the connected HDMI device that you could instead have it go to a bluetooth headset? This is assuming that bluetooth connectivity is possible for the Ras via USB or....etc
I also posted another thread looking at whether or not the plex client could do audio redirection to the iphone thereby allowing one to use the iphone with headphones to listen to a movie quietly.