Meanwhile, I have checked on her doc at least twice today... That one fella still just took off from the tower...
and that misplaced quotation mark is still there.
Not very. For a whole book, I might write where it starts, where it ends, then some in between notes of important stuff that happens in the book. For my last piece, I wrote down (like I was talking to myself) what I intended to do in the chapter I was working on. Because most of my stories are originally played out in my head long before they met my laptop, I also included a quick write-up of what the original story was. Then somewhere in the tab, I included some notes such as what I wanted to change, where I was going to go if I didn't stick with the original story, and other stuff like that.
I'm not professional by any means, and honestly, I'm clueless on what an outline's format should be. My outlines look more like random paragraphs written down, but they help keep my story on track so I don't get stuck on some line that'll go nowhere.
You don't necessarily need your story all sorted out, either. I have written a few stories that I just had some ideas of pit stops the characters where going to make and not every detail sorted out. And even still, on stories that I have already played through in my mind, I still might not know what's going to happen on the paper (especially with dialogue). Having an outline simply keeps the story on track and hopefully keeps it in a 70k word book instead of a 800k word book that publishers will raise an eyebrow at (and probably reject).