This is very cool! I don’t use KeyboardMaestro but have done a similar workflow for my weekly plan. I’m struggling though with the dates in icalbuddy - do you know of a way to use sort of relative dates, such as ‘use the closest Monday as the base date’?
I posted my question here, but no luck so far…maybe icalbuddy has fallen out of favourite (or been replaced with something better?). Would much appreciate any advice you might have!