Without disagreeing with you, I wonder whether it's possible (without true Artificial Intelligence) to consistently provide really useful error message, given the immense flexibility and power of even the simplest of programming languages (and the immense variety of ways a programmer can screw up).
Documentation, on the other hand, suffers from having been written from the perspective of the people creating the program, not the people using it. I don't know how to fix that, either.
@publius @mhoye if you use your own thing, and you hire or work with people who are not as familiar with the thing as you are, or you just occasionally read the top Stack Overflow questions about your thing, it becomes fairly obvious where the documentation and/or error messages need to be improved.
"For experts by experts" isn't a way to make software for anyone but yourself.