Playback Identical Audio to Multiple Devices

One way of accomplish this is to play the same audio stream through two mediums (analog & HDMI). See how to do that here: http://answers.microsoft.com/en-us/windows/forum/windows_7-pictures/is-it-possible-to-have-speakers-and-hdmi-play-at/4563a5f8-4be4-4463-b312-eff594a9ae49, answer reproduced below:

1. Open Sound panel
2. Select Speakers as the default playback device
3. Go to the "Recording" tab
4. Right click and enable "Show Disabled Devices"
5. A recording device called "Wave Out Mix", "Mono Mix" or "Stereo Mix" (this was my case) should appear
6. Right click on the new device and click "Enable"
7. Right click on the new device and click "Set as Default Device"
8. Double click on the new device to open the Properties window
9. Go to the "Listen" tab
10. Click on the "Listen to this device" checkbox
11. Select your HDMI device from the "Playback through this device" list

Then you can just connect the headset(s) to both the HDMI device (TV or monitor) and the analog (PC or Speakers) output.

To manage several microphones and speakers devices, we recommend Voicemeeter Banana, the virtual audio mixer for Windows specially made to route and mix several physical or virtual I/O. www.voicemeeter.com

My solution: voicemeeter. It does have a small overhead of up to 5% CPU usage, but the output is not delayed on any hardware device. It basically creates a virtual input that takes in the audio you would normally hear and then sends it to up to two hardware output devices.