Not sure if Luis is still interested in the post as Northwestern has shared their IBM Watson solution at InstructureCon 2018.
Not surprisingly, the first item as shown in their "Lessons Learned" slide indicates "It's a lot of work!!!". Indeed it requires a lot of investment to build an enterprise-level solution.
As for Lusis' original question, I can NOT answer the 2nd and 3rd parts.
But, for the 1st part, I personally feel very happy with a simple ChatBot to serve
The beauty of this kind of bot is that it requires zero technology background.
For sure, if one has some luxury to have certain programming skills, this kind of bot can be even published as a voice app right on your Windows 10 computers or mobile devices. So users can talk with the bot instead of typing only.
To make it clear, anyone can start testing it out by using Azure free account service. For Internet2 customers, the whole (basic) setup on Azure only costs several cents per month or less while it can be used anywhere including support web page and Canvas courses.
If interested, please see my (muted) demo at Arc. First 20 to 30 seconds will be good enough to give one a basic idea on how to use a bot in general support and Canvas courses.
For any institutions that uses ServiceNow or similar services, (local) Canvas support can be provided within ServiceNow instead of using this kind of simple bot. The agent transition (from virtual to live) is pretty slim.
If interested, I have a prototype (muted) demo on Arc. Please be aware that the video is about our course evaluation system integrated with Canvas.