- A lot of the code handling TODOs was written early when there were
  no plain lists.  That code often explicitly assumes that TODO is preceded
  by the beginning of a line and a few stars.  Several regular expressions
that are used all over the place implicitly make this assumption.

In outline mode there is the possibility to replace the stars with an reg-expression. That means you can replace the star as the headline-indicator. Maybe you can take some code from outline-mode.


- To make TODO in plain list items fully useful, I'd have to be able to
  apply tags to them.  However, other than headlines, the first line of a
  plain list item does not have a defined end, it can be filled and
  wrapped - so where would a good place be, where should TAGS be stored?
  Any good proposals?

maybe you can rise the importance of org-tags-column like in "if a ":" is here, than this is a tag.

Aside from that...

What is the basic design model for org-mode? What is org supposed to be? Where it is headed? I thought I got an outliner with dates-capabilities. No it's almost a full fledged publishing platform...

I think you did a terrific job so far. Maybe you have to make some fundamental decisions here...

Regards,
Christopher



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