Maybe I'll be more a crackpot like the person who made Temple OS and Holy C...
I'm not sure I should admit it, but having "grown up" on a Commodore 64, I actually understand exactly what that guy is talking about.
There's a feeling I think most programmers can relate to where you get into a super-productive groove. The language, libraries, and tools of your environment fade into the background and you feel like you are directly manipulating your software at a conceptual level. It usually takes a certain level of experience with an environment to be able to reach that state for anything significant. But I think there are environments that make this easier. E.g., scripting languages can remove the complications of compiling and linking. Dynamic runtime environment can be directly manipulated without building extra levels of abstractions by hand.
The C64 took the dynamic environment and transparency to a level you would hardly consider today (well, that guy does). Everything is memory-mapped and memory can be mapped directly to the screen where it can be examined and directly changed. Your program, runtime execution environment, data, graphics, sound, and other resources all live together in the same memory space. Sure, it's easy to screw everything up. But it's also very easy to reset and start again.
But that guy is a terrible communicator. Heh, he would frequently start a sentence, stop half way through and never finish it (I think he was completing his sentences in his head). That whole thing is interesting to me, but in the end I think he's pursuing an aesthetic goal that is very personal to him... that is, it's a creative piece of nostalgia that is a nice mashup of things he likes from various points in his life.
I should mention, I don't think of "crackpot" as a necessarily pejorative term. Mostly, all of us spend all our time trying to learn, understand and follow systems of knowledge and belief that large groups of other people are also trying to learn, understand, and follow. We're trying to follow the conventions of our society. I don't think there's anything wrong with that. In fact, it can often highly essential that we do this -- e.g.. you don't want anyone using novel traffic rules while you're trying to commute to work -- but if that's all *anyone* did, *ever* then there'd be little chance for anything to get any better.
Crackpot are the ones, at the substantial risks of failure and social cost of zagging when everyone else is zigging, that will try something different anyway.
Sure, they usually fail. But sometimes they succeed, and the next thing you know we are all zagging, and things are better than they used to be.