Most of the content on LW is historical content, where editor features like that weren’t available. I want to make sure the ToC works well for that content, but I feel hesitant to edit all the HTML of those posts, in case that does change the semantic meaning of the text in some cases (obviously we introduced some of that confusion already with the ToC, but I think editing the old content feels a bit more violating than that).
Also, I just want to point out that one obvious compromise would be to both treat all-bold elements as headings (for compatibility with as-yet-un-updated old content), and convert all-bold elements in newly-created content (that is written with the Draft.js editor) to proper headings. That way, you would not be creating any new standards-violating HTML, while not being under any pressure to edit old content, and having the ToC work as expected for said old content.
Also, I just want to point out that one obvious compromise would be to both treat all-bold elements as headings (for compatibility with as-yet-un-updated old content), and convert all-bold elements in newly-created content (that is written with the Draft.js editor) to proper headings. That way, you would not be creating any new standards-violating HTML, while not being under any pressure to edit old content, and having the ToC work as expected for said old content.
Oh, yeah. That’s what I meant to say above. Adding that behavior to our editor seems relatively low-cost.