> I think the problem with off-the-shelf solutions here is that these aren't flexible enough. Too true. I am using ready-made Loop Habit Tracker on Android (me

> I think the problem with off-the-shelf solutions here is that these aren't flexible enough. Too true. I am using ready-made Loop Habit Tracker on Android (mentioned in another comment), but I am slowly moving to track things inside Obsidian, which is free-form Markdown editor. Using Obsidian's Dataview plugin makes it really simple and has this advantage of being absolutely flexible that you mention is important. Doing it freehand inside Obsidian (with some prefilled templates and Dataview plugin) makes it really close to your CLI solution in terms of flexibility. Still, your solution sounds cool. :)