Hi Tony
Nice thoughts, or seeds of thoughts...
I confess I didn't take to TWOutlier when it first came out. It was at the same time as a conversation on TW as an outliner, so I was judging it on those merits, and not seeing other possibilities for it. It took until I had been working in StackEdit and really liking the TOC on the side there, and frustrated by StackEdit's limitations in other areas.
Because of StackEdit, I also got more used to the idea of editing while seeing one thing, and creating an end result that looked quite different, and better, than the editor does. So when I looked at TWOutlier again, it had the potential of the TOC I liked from StackEdit, plus it occurred to me, as I doubt it would have before, to do the editing in TWOutlier, and have the web viewer be in a regular vertical TOC tiddler.