1.) The people who can do this aren't going to do it for 30k or $10/hr. Properly solving this problem requires an understanding of tech and the development process, pedagogy/communication/instructional design, and information management. Lacking any one of those would result in a system that's an unusable vanity project. I have a couple of decades of small-shop coding experience, experience as an instructional designer at an Ivy, and graduate education in information management, but if you want me to use all of those it's going to cost you and companies are resistant to that. (See: How a lot of non tech product companies treat their IT teams since they don't generate revenue). Now imagine if the project were led by someone more qualified, which it should be for a company of your size.
2.) Most companies don't have a culture which would allow this to be done well. This is the sort of work which requires both a lot of honesty and a lot of careful planning. A lot of information ends up hidden or inaccessible due to people's egos, or executives not being able to handle the information so it's buried. People need to be honest about their workflows and what they don't understand, and they need to feel comfortable being honest about such things. This gets really messy. On the dev side, a common cultural issue is "I had to learn it, they should too" or the urge to make understanding the complexities into a shibboleth for the in-group.
So I agree with you, but it's unlikely to change soon in my opinion.