Last night I have been playing with a minor mode to enable a checkbox in a heading, or rather to fake a checkbox. To be honest, it was a 10 minute job. Took me way moare time to figure out avialable key combination to use (which I didn't found). In general, enable mode and use S+up/down to toggle a checkbox. A heading with a checkbox is of form [ \t]*\\*+.*? followed by a [ ] or [x] before a heading. It means a [ ] can be placed somewhere after the leading stars, whitespaces ignored. This has nothing todo with my previous hacks of todo keywords. This one does not uses todo states at all so it can be used with todo states. It is just a small prototype. I will use something else than replace-string later on. Just wonder if the approach is sane. There is also a repo on gh for interested one: https://github.com/amno1/org-heading-checkbox