I don't resile from my original comments, a chat bot would be nice, but why go to the extreme of making one? If I had a lot of people requiring it, and a large organization behind them, sure, it would be worth it. Most education organizations would, I suspect, have a teacher/student ratio of about 1:25, some lower and many more, higher. So the point at which the development of a chat bot to use in Moodle becomes a cost-effective solution is when? 100 staff? 200?
Really, this is an old, old problem, and exists for every software package ever released, not just a Moodle problem. How about simply making videos of the most common problems and allow staff to access them? Would that not help people more if they have direct access to the information they need?
Moodle doesn't change everything every new release. I am still uploading files the same way I did when v2.1 was released. I still add activities the same way. I added a disclaimer to a video on an old site I used to admin which said something like "This video contains up to date information on how to upload files to this Moodle, from v2.2 and forward. The video will change when the process changes. Any differences in appearance may result from changing the Theme, but the process will remain the same." I unashamedly pinched an older term from a former Moodle employee, really tall, very clever and really nice guy (I forget his name) and called the series "2 Minute Moodles". I hope the people who took over the Moodle kept them going, but I haven't heard. I do the same things now, have accessible, comprehensive, short and single pointed videos. I am also adding the videos I am finding that are connected to the Moodle Docs that explain stuff, when I don't have time to make one. I am placing these videos into a single course for staff to access when they need them.
So I have to ask, where is the need for a chat bot here?
EDIT: The key is cost effectiveness. When making, using, training a chat-bot becomes a more cost effective solution, i.e. cheaper and easier than making videos, sure, I'll change my approach, but I suspect that won't be for a while yet.