I was recently made aware of a video by Tâches Teaches that is very good. It shows automating Bitwig digital audio editor, but many of the ideas would work well with other applications.
If you're looking for a tutorial/overview of how you might set up automation for a relatively complex application, check it out.
I should just point out that I was the one who recommended KM to Tâches 
He then took the ball and ran with it further than I could have imagined! I especially liked his idea of using the Trigger Macro by Name which he assigned to (I think) Cmd F. Instead, I adopted the Command Pallet approach used by many IDEs, and assigned it to Shift Cmd P. It certainly saves having to dream up unused key combinations for each macro