The actual first day of streaming
Day one in the books. I was trying to save the video at the best format possible while streaming at a pretty good quality, but this ended up making the stream really choppy. After getting feedback from RedAngle, I fixed the video. As described in the Chris Cornell post, I wasn't trying to make the stream perfect, I was just trying to get online.
Finally got the audio working pretty well. The current setup is using Airfoil to transmit the audio from the ProTools PC and then Airfoil and Loopback to receive the audio on the streaming PC. Here is a visual of my setup: