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This is an interesting idea and I can see how it might be useful. But I wonder if displaying items "bottom-up" instead of "top-down" (i.e. conventional outline/tree-based behavior) might be confusing, especially for new users.

I wish there were some way to try it out. I think that'd give me a better idea of whether it's something I'd like or not.

AFAIK, there's no preference to enable this kind of behavior.