Nice idea!
I wanted to automate getting an email from Outlook to MLO so I wrote a
macro in AHK (AutoHotkey) that, after you click on an email in
Outlook, automatically drags and drops an email from Outlook into MLO
and then assigns a context and a time spent based on a couple of mouse
clicks you did while in Outlook.
If you had Outlook assign a category and move it to a folder, I could
modify my macro to have it also assign/create a context for that
Category