Have I worked before? Been in the industry for almost 25 years now.
The benefits from complex software should be so disproportionately massive that the users would be willing to adopt it. The C++ language and the compilers come to mind: they do come with documentation, are complex, but that's nothing compared to the entire worlds that you can create with C++.
On the other side of the spectrum you have things like Parallels Plesk: an awful piece of software that always creates more problems for you than it's trying to solve, even if you read their tomes of documentation, knowledge bases, searched their forums etc. The existence of Plesk and software alike can't be justified really.
