I've put together this 15 minute video that summarizes the problems that need to be solved and paints a picture of what an Outside-In UI could look like and what you could do with it.
There are lots of details I couldn't go into within the limited time span of this video. The intent was not to present a finished design. Rather, my hope is that the video can help the community find new answers to difficult problems by introducing new questions to ask. It's an attempt to break out of some old assumptions about how things are done in Drupal.