Document Automation is a great idea, but you can spend a million dollars automating a complex document (the cost is the highly knowledgable document automation experts). What if you could just explain it to a ML that understood.
“Include this paragraph if section 21.2(a) is included”
“Use this block if the user is a ‘Person'”
It would be “chatty”, and would reply with what it’s doing. It might be difficult to maintain though since you can’t “see” what it’s doing. Maybe that’s OK? Maybe you can ask it to tell you what relationships a particular paragraph or section has.