I'm new here and a bit late to the party but you might be able to do bullet 3 (Intelligent alert system) by interacting with the Rescuetime API. It's already set up to track what you do and how productive it is. You could just tack an alert system on top of it. Maybe?...

And I like your "Odd ideas." I was a social coach for some time and always tried to brainstorm ways to help clients remotely or, even better, automatically by recognizing speech patterns, pitch, inflection, even body positions using like a Zephyr Bioharness or something.