The enhanced outlining in WordPerfect 3.5e uses Control-Return for Outline Return (new topic with new label), Control-Tab for Outline Tab (tabs the current topic and its subtopics one tab stop), and Control-Shift-Tab for Outline Back Tab (back tabs the current topic and subtopics).
In its most recent OS versions, Apple has designated Control-Tab for another use. So here are some new macros that reassign Outline Return to Option-Return, Outline Tab to Option-Tab (except when the cursor is in a table; then it produces a Table Tab), and Outline Back Tab to Option-Shift-Tab. However, you can easily reassign the outlining commands to any other keystrokes.
Other macros are included too: Auto ¶ Number adds an automatic (self-updating as you edit) number to the start of a paragraph, followed by an indent. Auto ¶ Number with Restart is the same but restarts numbering. Outlining Label Set changes label styles to standard academic format. Outlining Toggle displays or hides the Outlining Bar.
The ezine "About This Particular Macintosh" said WP's enhanced outlining was "rather amazing macros" and it "could be the most writer-friendly outliner available." Now it's even better.
Free in the Files section here, as Outlining Keystrokes 2.0.sit.