I'm also trying to set something up, and some of the challenges involved in the Mostly Walking setup relate directly to what I'm trying to do. Right now, the question I'm specifically looking for an answer to is:
How do I send game video and audio to a friend with no lag? (Or at least, extremely minimal lag.)
I couldn't remember if Sean ever specifically mentioned how he does it, so I'm glad you mentioned your experience trying Skype. I'm curious - what specifically did you find unsatisfactory about Skype (aside from what sounds like an overly difficult setup on your end)? Quality? Lag? Complication for people on other end to setup? Anything else? I thought about trying Google Hangouts, but from what I've read on various other forums it sounds like that wouldn't be any better.
I don't even need to send or record any webcam or microphone signals at the moment. For what I'm doing, I plan to be in a regular phone call with a friend. I just want him to be able to see/hear the game I'm playing as close to real-time as possible so we can 'play together', in a sense. Streaming to Twitch or the Steam client seems to carry at least a 15 to 20 sec delay, and that's not going to make for a very enjoyable experience on either end.
For reference, I'm playing on a PC. So something like "PS4 Share" isn't an option.
I'll report back if I learn anything helpful, and likewise I'll be checking this thread for any helpful replies.