This last round of discussion make me think that this might not be the right UX to achieve our goal here. However I won't have time to elaborate much more because (1) I need some quiet time to think about it more (2) writing the ideas down will probably cost me multiple hours, hours that I currently do not have as the Windows/py3 testing and issue6528/6538 have been time consuming. I'll come back to you about that.
Actually, do you mind sharing at least sentence or so about what you think might be the right UX, even if it's not completely clear to you yet? I just want to get a sense of what you have in mind.