>I think the whole thing is wishful thinking. What I need from you guys is input. Is what he wants possible? Under what circumstances?

Think about what it would take to do this manually.

Set up a bank of (Indian?) tech support guys monitoring 5 screens at a time to follow along silently while your user works.
You would need a lot guys, and they would have to change up who they are watching periodicallyto prevent devastating boredom.
Eventually, one of them notices a user fiddling around.
He has to decide if the user is "in trouble" or just normal working.

(All the steps to this point require human understanding and intelligence, not possible with any kind of AI)

If you think about it, even a human could not figure it out from just watching.
He would need to have the user talk to him about what he is trying to do.

This decision also requires understanding this particular user:
What is his ability in this task?
What is his capacity for frustration?
Some users are happy to figure stuff out on their own, some would be very annoyed to have Clippy pop up and offer help.

Assuming you could actually decide if the user is "in trouble", now you need to offer reasonable assistance.

Your theoretical help desk guy cannot be expert on every nuance of Word, Excel, FoxPro, C#, Powerpoint, etc.
So, now he has to know who can help him with this user.

This project is deeply into the realm of "not even theoretically possible"
You can't make software that can think and reason - not possible.

These specs seem to assume that software can think and reason, and do so much better than an expert human.

The only person on the planet who can know if that user is "in trouble" is that user.
He should just call the help desk when he needs help ;)

Did he send these specs to you on April 1st?