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.