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


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