This looks really cool! My only suggestion is to not have different “levels” of heading and just have only h1; the stuff that logically appears under this heading should then be syntactically underneath it (i.e. these should be children); this has the benefit of not only making the outline more semantic, but also making the section collapsible. This seems to me to be the best way to integrate heading-style formatting into the outline model, as opposed to inheriting features of Markdown or HTML that do not make much sense in the outline model.
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