UPDATE: I figured it out, you MUST name the Hook Box (and Widget Area) for it to work. Because I was just testing I did not name the Hook Box. So, if anyone else has this issue, NAME YOUR BOX!
Working on a .local site I had some goofy stuff going on with both Custom Widget Areas and Hook Boxes, but on a live site I can not reproduce the Widget Area issues, but I can reproduce the Hook Box problem... it no hookie for me.
I watched Eric's video and it all seemed straight forward, so what am I doing wrong?
Video from online site: https://cl.ly/2aedee6284cf