A few things about YouTube's processing system;
1. I prefer the older system, where it only uploaded one at a time; it'd them move on to the next video upload while the system process the last video. When the video is 100% uploaded and moves to processing, when processing it has its URL address and its place in line on the channel. There's a few other things I miss with their older system, but we'll never get those back either. Google fucking fixes ruins everything they touch.
2. The newer system allows multiple (up to 3, IIRC) videos to be uploaded at once; this can easily lead to uploads not being in proper orders. Though if your videos are mostly of the same length/size, you can stagger their upload by 15 minutes or so to get a nice proper order. And as Phil said, you can set a specific time for the video to go live, which you can use to set a specific video order.
3. Phil thinking people should watch all his videos in a play-list and not point and click on specific videos shows he doesn't understand the platform or the basic user; especially saying the person's solution is built around people using YouTube improperly. Phil, you don't fucking know how to use YouTube and you have a "10+ year legacy."
4. Phil could easily create a thumbnail for his streams; but the man who knows how to use YouTube properly won't.