So many good words, but they all miss the crucial point: you can't write a parser for org-mode. So elisp interpreted is needed to run the lisp code that defines it. It means that org-mode can be good while you are using it from emacs, and it sucks for anything else. I use markdown now, because you have a lot of tools to deal with markdown, while all tools for org-mode are bound to emacs. Which is perfectly fits the e…
I think the trick with Emacs and Org is to stick to the basics and then only add features or change your configuration very slowly, as needed. I have been using Emacs non-stop for >20 years and my .emacs is just 20 LOC. It's been shrinking, not growing. My goal is to bring it down towards 0 LOC. I have committed a few things upstream to modernize defaults.
Personally, I think the reputation of Org, Emacs, or Nix being hard and complex is undeserved. It's rather a documentation problem. There's no simple documentation to onboard newcomers and show them the basics in a principled way. So it looks like a mess, but it isn't.