This was a really helpful walk-through Chris. I agree with your point in the IndieWeb podcast that it could be compressed into half an hour, but I always thought that was the point of adjusting the playback speeds?
I just had a few thoughts / questions while watching / listening:

I never realised that I could add all my Rel=Me links within my profile, does that mean that I do not have to go through all the rigmarole of adding them to my ‘child theme’? That definitely makes it a lot easier to setup.

I am really interested in modifying / developing a custom post kind, but what happens when David Shanske updates the plugin? How do I set up to allow for updates and customisation? Is this some sort of ‘child theme’?

I wonder if it were possible (maybe in the IndieWeb multisite or something) to customise the ‘Welcome’ box when you first start WordPress? Imagine if the information that is detailed in the IndieWeb plugin area could be placed there, front and centre?