There should be integration tests for documentation.
Maybe some machine learning could be applied to that?
Maybe I should set that up on some cloud service.
Let me check the documentation for how to do that...
That's biting off way too much. You have to realize the scope of the actual problem "making humans understand something they previously do not understand". If you can do that you might as well apply it to fixing education instead.
One of the things sandstorm.io does which makes a lot of sense, is that they regularly commit changes to their docs within the PRs that change the actual software. It's not integration tested, mind you, but the general practice means they do a pretty good job keeping their docs updated.
