Hi David, > Is there a documented requirement of the order of things in a Org > outline?
Yes. See https://orgmode.org/worg/dev/org-syntax.html. > For instance, do these things have to come directly after the > headline and, if so, in what order? Will Org get confused otherwise? This is possible, I guess. I recommend you follow the link above. But to be explicit: the expected order is: HEADLINE PLANNING PROPERTYDRAWER where PLANNING and PROPERTYDRAWER are optional each. Timestamps may occur in the HEADLINE, in the PROPERTYDRAWER and below. You may also consider to use M-x org-lint in you Org file to check these requirements (and more.) HTH, Marco