Some good ideas there. I thought about something very similar to what you suggest for a job selector button, and the dialog engine should eventually get just such an overhaul, along with the rest of the scripting system.
I like the idea of replacing "event" with a short description, and might see if I can fit that into my worklist. The girl details idea is nice, but probably a bit more work than I have a mandate for right now.
I won't comment on adding columns into tables, since that's Dagoth's code