These are guides to the various ways we've found to stream audio/video content for the group.

I stream movies and anime through discord using a particular hardware setup. I settled on this after some trial and error and some consideration of my goals. I wanted to:

1. Watch from bed
2. Hear the video AND still hear people commenting
3. Have a good experience for people who are into the video

To do this, I use headphones AND monitor speakers.

Initial setup/configuration:
I set Discord to use the headphones for input and output, and have the input mode set to voice activity. (Settings / Voice & Video)
On my video player (I generally use DVDFab Player 6) I've set the output to the monitor speakers.

Before Streaming: (Initial Setup)
First, I join the Discord channel and start my camera so I can talk to everybody.
Then I select the video (file or disc) and start the player (Immediately pausing if it starts to play)
Then I share the player application as a stream (I've found 720/30 works really well for my internet connection)
If Discord can't share the player, I have to go into Discord's Settings / Activity Status and remove the “game” and re-add the player.

Starting the Stream:
In Discord I turn off my camera (it just sucks bandwidth/CPU and no one should be looking at each other anyway while we watch the movie, right
Then I set Discord's input mode to “push to talk”. That way, sounds in my room don't get transmitted over Discord.
Then I start the player so we're watching the movie.
Then I move one headphone so one is on my ear, and one is off so I can hear the movie through the monitor speakers (because I can't hear my own stream through discord).
Finally I adjust my monitor speakers to a good volume… and we're watching the movie!

Finishing Up:
Once the video is over, I basically reverse everything.
I set Discord's input mode back to Voice Activity.
And I turn on my camera so we can talk about what we just watched.