> That only matters if you want to use the more interactive features of Emacs' org-mode. I only use Vim and still write everything in .org files.

I did something similar for awhile but felt like I was net negative in effort to gains.

> In the end Markdown isn't bad, but I don't like how basically every platform and tool adds their own special flavor.

Yeah I stick to a known safe subset, including legacy newline behavior, and only a few extensions to that. (highlight and checkbox off the top of my head)