I think my issue is more about the sharing, the whole outlining process is what I use outliner for.
Though I am curious on what you are struggling with and the reason to export to Word if you are only using Word to style it up at the end?
I have many times successfully exported to Word as an outline (you can even start your outline in Word). Once it is in there you can fiddle with the styles and get whatever result you need. My problems was then getting that back into a format that doesn’t remove the “outline” structure.
Since writing my original post I have had some developments. Though like any workflow I am having to test it in the real world and want to get it right before i pass it on.
The key is with markdown files. Basically, if you can import and export to markdown then you can do import and export to anything.
But it is not easy, and lots of custom services and little apps all do different things.
And of course, once it is in HTML you can style it however you want.
For instance you can export to OPML from Omnioutliner, you can also export to MMD (a variation on markdown). MMD to Word, Word to MMD, copy as MMD then paste to HTML, or OPML…
It is a bit crazy, but I am making progress and there are loads of great resources out there. Being able to copy out of Word and paste as is already a huge step forward. There is also a script for Google Docs that converts to markdown.
I have found that you can give a MD file to a client and walk them through why they need to section content and demonstrate how it makes marking up in HTML so much easier than Word. As simple as basic HTML is, for someone who has never seen it, it can be intimidating. Yet a few hash marks and hyphens are for more familiar.
But sadly, when people use Word as a typewriter and not even define things as headings (they just make them bod and individually make the text size bigger) it is always going to be a problem.
Alas, the MS Office way of working is something you are brainwashed with, and it is here to stay.
It is so sad that something as simple as markdown and opml can be so flexible, and free, yet companies still invest is buggy bloated software and then the training courses and support required to maintain them.
Markdown has genuinely changed the way I do so many things, from note taking to making websites. But it is still a little convoluted at the moment. But I hope to be able to share once I have grasped it myself.
… I will return when I have it sorted :)