This is all good feedback, thanks. Couple of things are work here:
First I like that in current design text selection is maintained if you hit escape twice. (for example select a word and then hit escape twice) That means that I don’t really want to change things so that cursor is always placed in specific location when exiting outline mode.
Second I think eventually this could be solved with more commands in outline mode. For example maybe VI style i to exit outline mode and move selection to start… but I want to avoid adding any such commands right now until I have a better idea of what I want outline mode to become.
One hack right now is that if you are in outline mode Command-Left/Right will still move your caret to start/end of line. Then if you exit outline mode cursor will be in that location. This isn’t really by design and might change in future… but maybe useful now.
I think for now I can more easily address the problem by just making outline mode more obvious and distinct from text mode. In earlier beta’s I used a different color. Maybe I will try that again, or maybe I will try drawing a darker borer around outline mode rects.
Does that seem reasonable for now?