I'm doubtful it will ever work (but I'm glad someone like Bret is working on it). If I think about the technical things I've learned the hard part is usually learning how to think about them, not telling a computer what to do. Even in a low-level language like C++ it is generally not too hard to express what you want once you know what that is.

Now, it might appear that the tools Bret is working on help you to think about your problem better, and I think that's true at the margin. But they don't seem to help that much since mostly people are lazy and don't want to think hard (myself included a lot of the time). So these tools slightly lower the activation energy and probably somewhat increase the number of people who are able to learn certain concepts, but they don't lower it that much and a motivated person can generally find a good explanation of anything that's not at the research frontier.