Hi Martin,

This is a huge issue.[1]

Here is what I do to try to work around it.

I use git, to limit the damage from confusion.

I expand the entire buffer if I think I am about to be confused.

;;i like the idea of clustering undo but find it disconcerting
(setf org-self-insert-cluster-for-undo nil)
;;somebody, I think Carsten, suggested this, and it might work for
you, but for some reason I commented it out.  I don't remember what
the reason was.  Maybe speed.
'(defadvice undo (after org-undo-reveal activate)
 "Make point and context visible after an undo command in Org-mode."
 (and (org-mode-p) (org-reveal)))
;;(ad-unadvise 'undo)


[1]  It is even more important when combined with what is IMO Emacs's
greatest need for improvement, which is that you can undo, and undo an
undo, and this is considered to be sufficient since you can get
anywhere in the timeline in principle -- but many users, myself
included, prefer a true redo command, both because undoing an undo
does not let you do commands (such as copying) in the middle of an
undo sequence without going the other direction, and because it feels
more intuitive to tell emacs where in the timeline we want to go, and
go forward or backward if we overshoot, thus making it possible to
view the timeline the same way as we go backward and forward in any
linear sequence.  (redo.el provides the functionality, but it corrupts
the buffer.)  Of course, many are comfortable with the traditional
undo-the-undo mechanism, so that should stay possible, but there are
many who are not, and a redo mechanism would satisfy them.  It is
possible to get more fancy with a tree.

-- 
Myalgic encephalomyelitis makes you die decades early (Jason
et al. 2006) and suffer severely.  Conflicts of interest are
destroying research. What people "know" is wrong. Silence = death.
http://www.meactionuk.org.uk/What_Is_ME_What_Is_CFS.htm


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