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Unless I misunderstand, this doesn't answer my question. This tells me how to output the same signal to two or more devices. I would like to output one signal (plex/vlc) via hdmi, while also playing music in iTunes through USB

As per my edit, set plex to output from HDMI in its own settings and mac mini in general should be set to output from USB.
 
The one with an integrated DAC:) I think many modern amp's started to have this. For old amps, you can use an external DAC which will connect to your USB port, and increase the sound quality from your digital music files significantly. Mine is a Hegel H300, check out http://www.hegel.com

Thanks, I have seen those, just never considered that. Learn something new on here everyday.
 
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