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Re:StrictMark: Markdown, Refactored by codethief on Friday January 29, 2021 @01:37PM (#25960695)
> 1) the use of # rather than underline for headings.

While in theory I understand the appeal of the "WYSIWYG" syntax of underlining headings, in practice I've always found it less readable than expected. Consider, for instance:

    I am a paragraph belonging to the previous section but it looks like the heading belongs to me.


    I am a heading indicating a new section
    =======================================

    I am a paragraph belonging to the heading but the heading is weirdly separated from me.

    I am another paragraph belonging to the heading.

In some editors/IDE, the underline even gets highlighted / boldfaced, thereby exacerbating this effect.
Re:StrictMark: Markdown, Refactored by chipotle_coyote on Friday January 29, 2021 @01:51PM (#25960842)
I very rarely see this style -- which comes from "Setext", IIRC, which might be patient zero of the "human readable plain text markup styles" -- in the wild anymore, and I suspect it's probably for the reasons you're describing here. I almost never use it myself, except in contexts where the "source file" is just as likely to be read as a rendered HTML version. README files are a good example.

> In some editors/IDE, the underline even gets highlighted / boldfaced, thereby exacerbating this effect.

I think a lot of editors just don't know about this style of heading, but they do know that a line of three or more dashes is used to create a horizontal rule, so they're trying to highlight that.

Re:StrictMark: Markdown, Refactored by cannam on Friday January 29, 2021 @03:57PM (#25962446)
I had never heard of Setext! I do know that, before Markdown became popular, lots of programmers had their own similar format going on - this was mine, from 1998:

Perl program https://sourceforge.net/p/rosegarden/code/HEAD/tree//branche...

Documentation https://sourceforge.net/p/rosegarden/code/HEAD/tree//branche...

I wonder now how much of this was picked up unknowingly from Setext-derived documents.