"It looks like you want to create an application." Clippy lives!

>I have a client who has asked me to provide input on the feasibility of designing an application that would be an automated help desk kind of thing.
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>What he described to me was a software component that would automatically detect when the user is having trouble, and then provide the appropriate assistance. Some examples are - working in Excel and trying to get cells frozen, not be successful, and this application suddenly pops up saying "I see you're trying to freeze cells. Let me show you how". This same app could detect that you’re looking to pay by credit card, not check, on Amazon, and help guide you through the steps to do it. Of course what he's talking about is some form of AI that could provide any help on any issue.
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>What he has asked me to provide is a document outlining the percentages of success given different levels of resources. So, given 10 developers, the necessary equipment, and say 5 years, what is the chance of success. Then list the same given 20 developers, etc…
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>The closest thing to what he wants that I could see being possible is some wizard style application that walks the user through a series of questions to help determine the issue, then use this input to formulate a solution. It would be similar to Windows Troubleshooter, only smarter.
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>I think the whole thing is wishful thinking. What I need from you guys is input. Is what he wants possible? Under what circumstances? How much would it cost? How many programmers would it take? And, what I really need to know it, what are the relevant technologies needed to make this happen?
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>Thanks.