Mind sharing your Obsidian workflow? As someone who installed Keyboard Maestro for the first time 3 hours ago it's not immediately apparent how to do this :D
* switch to Specific Application -> Obsidian
* pause until... application "Obsidian" is at the front
* type keystroke -> Cmd+Option+D ; go to daily page
* type keystroke -> Cmd+DownArrow ; move cursor to the bottom
* type keystroke -> Return ; start new bullet in existing list