I fully see your point, his decision not to use any graphics library at all is also my biggest problem with his project simply because I wouldn't really want to do that and therefore a huge portion of his streams will only be interesting to me in an academic manner, so to speak. However, he's a really experienced programmer both in general terms as well as regarding working with the windows API (even though he really hates it because, as you say, it is a pain in the ass, no matter what you wanna do with it), so I assume he knows what he's getting himself into.
I'm howeve really interested in how somebody who's got a lot of experience not only in programming in general but also in games programming approaches such a huge project all by himself.