[TheCPT]

Yes, it can be done, even if you have them in MS Word "Outline Numbered" format rather than the nicer "Outline View". It is cumbersome, and imperfect, but beats doing by hand. I've tried both ways. :-(

[And of course, if you were smart enough to put your outlines in "Outline View" to begin with, then by all means use the ReadTree ap that is available on the board here and seems to work for many combinations of Word/OSX.]

Anyhow, here are the instructions:

1. Begin with a "Numbered Outline" in MS Word, normal or page view.
   
2. Remove any extraneous lines that are not part of the outline (i.e., did you insert a few lines to smooth out pagination? are there some at the beginning or end of the outline? these will turn into level one headings if you don't remove them; do this well to reduce problems in the cleanup stage; seriously, this is the source of 90 percent of my cleanup)
   
3. Select the entire outline and switch from "numbered" to "bullets" with a formatting button (it is easier to block delete bullets, even of multiple formats, than numbers)
   
4. Copy the entire document
   
5. Paste it into an empty blank rich text email in Apple Mail
   
6. Then click the "convert to plain text" button, or access it through the "Format" pull down menu. This both creates a tab delimited beginning to each line (that OO will handle well) and standardizes the bullets from the 5 or graphical formats that MS Word probably put in there
   
7. Delete the bullets AND THE HARD-TO-SEE "TAB" THAT FOLLOWS THEM with search and replace function. Thus, put your curser to the left of the first heading (i.e., to the left of "Introduction" on most of mine). Hold down shift and tap the left arrow twice, first selecting the tab, then the bullet; copy all of that, open a find/replace window (command-F), paste that bullet and tab in the "find" field, leave the "replace with" field empty, then "replace all"
   

   You now have your outline with a variable number of tabs in front of each level of outline entry

8. Then copy the body of your email.
   
9. Then paste it into a new OmniOutliner document in which you are not selecting anything (otherwise, if you are editing a row, it inserts it as part of that row). "Paste with current style" if you have a style sheet that you'd like to use in your default
   

No, not easy, but easier than importing the raw text and manually recreating the hierarchy.

Hopefully that helps at least one person. It took me forever to figure out. :-)

[And presumably the instructions above are something someone can script, but I've gotten my last set of course notes out of Word now, and hope that OPML standards are here to stay...]