Good points, since I'm an outlining freak. The best, of course, was Ecco Pro. But since its demise, the best to come along was Microsoft OneNote. Each tab in OneNote will hold about 60,000 words, and while they don't convert well inside of Word (ironic!), they do convert pretty accurately everywhere else using copy and paste. Inevitably, if you're going to use a word processor's outlining feature to outline a complex document, you'd probably be better off outlining it using another app and building your document using Master documents to gain more control over editing and its ultimate form.