I get the impression that he's a little out of his depth with this psycho-philosophical stuff.
He is. I've watched others of his videos over time, and I always get that same feeling. He just says he is knowledgeable, but when it comes to the nitty-gritty, that's where he often falls apart. Other things he "knows" but fails to understand them in their greater context and significance, especially things relating to GD lore (and of course, Quabalah).
If you want to see some great comedy, try watching his review of the Book of Thoth. He looks as of he's leafing through it for the first time, really he does. I could overlook the mumbling (I stutter myself, I know how speech impediments work) if there was anything of worth behind it, but every time I watch him I find myself banging my head against a wall.
Both of the above videos just display a deplorable lack of understanding of what the Tree is, why it is, and how it works. One does not escape the Tree any more than one escapes a map of the world by taking a walk around the neighborhood. He also seems to have a limited, derogatory view of magicians, and his insistence on that point is just plain weired.