What about when the alternative to the software also requires training? For example, draftsmen didn't intuitively know how to create usable architectural or mac

What about when the alternative to the software also requires training? For example, draftsmen didn't intuitively know how to create usable architectural or machine drawings; is it so horrible that today they have to be trained in the use of CAD software, instead of being trained in pencil and pen drafting? If you're performing a complicated task, it's reasonable to ask that the software not make the task harder, but it's also reasonable to expect to have to learn how to use a new tool. I suspect that project management (at least for some large projects) may be such a problem domain, where the tools are unavoidably complex.