| I'm sure these are great technological answers but this problem can be solved simply and quickly by a human. Not every issue needs to be solved by a butter robot. Why not employ a technical writer/documenter/whatever job title you like, even as a temp, whose sole job is to sort out the mess of documentation you have and then to write new documentation as you move forward? |
Primarily because it's a far, far more complicated job than that and you can't really hire someone off the street to do it effectively. Typically in a tech company a tech writer is going to know almost as much or more (after years of experience diving into every detail) about a given technology or application or API, and so that begs the question why not make twice as much working as a software developer and not have to sort out these types of messes?
Also job security. Anyone doing this work full-time is the first on the chopping block, and developers who are working on documentation tend to be perceived as lower status since they aren't delivering features.