100% agree with the trigger being the hard part, and with wanting the observer robot. I know there are partial solutions (RescueTime is a big one) which watch your text editor, or watch your web browser, or suck in meeting data from your calendar, but I've never really been that happy with them.

The further complicating wrinkle for me personally is that I work at a robotics company, so I spend a bunch of time at ssh terminals to remote machines (robots, shared VMs, etc) where it is neither practical nor desirable to install vim plugins hooked up to my personal time tracking setup.

So I'd love for the observer to be able to be able to also watch my remote shell sessions and record things like which file paths I'm editing and commands I'm invoking, from which I could fairly easily construct rules about which general problem area I'm working in.