Edit: Now that I understand the question...
How about something like the following nippet of code. It seems to work for me, though I haven't figured out how to avoid being prompted for the file local variable every time.
(defvar omm-state nil
"file local variable storing outline overlays")
(defun omm-state-mode (&optional arg)
"poor man's minor mode to re-apply the outline overlays "
(interactive)
(omm-re-enable-outline-state)
(add-hook 'before-save-hook 'omm-state-save))
(defun omm-get-all-overlays ()
"return a list of outline information for all the current buffer"
(save-excursion
(let ((all-overlays (overlays-in (point-min) (point-max))))
(mapcar (lambda (o)
(list (overlay-start o) (overlay-end o) (overlay-get o 'invisible)))
(reverse all-overlays)))))
(defun omm-re-enable-outline-state (&optional arg)
"turn on outline-minor-mode and re-apply the outline information"
(outline-minor-mode 1)
(when (listp omm-state)
(mapcar (lambda (p)
(apply 'outline-flag-region p))
omm-state)))
(defun omm-state-save ()
"save the outline state in a file local variable
Note: this just replaces the existing value, you need to start
it off by adding something like this to your file:
# Local Variables:
# omm-state:()
# mode:omm-state
# End:
"
(ignore-errors
(save-excursion
(goto-char (point-max))
(when (search-backward "omm-state:" nil t)
(goto-char (match-end 0))
(kill-sexp)
(princ (omm-get-all-overlays) (current-buffer)))))
nil)
This solution requires you "seeding" your file with something like:
# Local Variables:
# omm-state:()
# mode:omm-state
# End: