lol this is a great wording for something I've not been able to express before
I sometimes wonder... is it Markdown's specification chaos the reason for its success? Maybe it was just barely enough spec to be usable but also small enough to allow anyone to make an implementation that seemed right. No qualifications to fail. Thus, it proliferated.
The xkcd[1] problem is a darn shame, though. At least CommonMark exists for people who want to point to a "Standard"
HTML and CSS were also chaotic at one point and it sucked ass.
Loosy goosy is fine for a hobby project but if you do anything with vanilla Markdown beyond simple links, headings and text, you quickly find yourself in a frustrating zone of incompatible hacks and syntax extensions.
Markdown succeeded because both the source code and the rendered HTML are readable. Other markups like restructured text don't look good in source form.
But ya, in order to look good in source form, but still handle arbitrary content, they had to add all these little exceptions and corner cases.
Yeah I ultimately can't hate markdown, but it really was just specified more or less as "whatever markdown.pl does", and markdown.pl was not exactly the most rigorously engineered thing. Even bbcode of all things has more predictable structure to it. The commonmark/pandoc guy now has Djot, which is supposed to be a bit more sane, but I get the feeling it's probably too late :-/
Markdown is definitely a case of “worse is better” and it helped that it was half-canonicalizing ASCII formatting workarounds that had been in common use for decades.
And Standard Markdown / Common Markdown / CommonMark was subject to a bunch of drama when it first emerged:
https://news.ycombinator.com/item?id=8271327
I generally like John Gruber and have been a DF reader for years, but I really never understood his perspective on this; I have trouble seeing it as much more than a "worse is better" kind of take.