Well, technically, if you are going back and forth between your outline and your first draft, then you haven't outlined it properly, or you have started writing too soon. You need to re-think the purpose and content of your outline.

Outlines serve two purposes: a way of formatting my arguments (not unlike in philosophy with premises P1, P2, P3 leading to conclusion C, etc) and as a jumping-off point. But there's a thousand ways to write a certain statement, tell a part of my story or explain a concept. I usually figure those out during the writing process and can't imagine knowing that beforehand. It's like guessing where to put your furniture when you haven't built a house yet - the details matter, but they are dependent on the larger structure that it's very hard to get right so early on. Plus, I often think of new arguments or points of view during my writing, necessitating restructuring or rewriting of parts. Do you not have those issues, or are they not significant for you?

But it is a bottomless black hole pit of despair unless you get professional training on it.

InDesign so far has been me attempting to cobble together a few booklets. If I embed all the assets, I don't break everything. Its logic is kinda weird and I don't know whether that's because of my low skill level, because I confuse concepts with Illustrator and Photoshop, because it's just weird or all of the above.