As for your orgmode example, it's not a very good example of "just plaintext" if the metadata code in between the bits of text is larger than the content of the note. I imagine that with nice syntax highlighting it becomes easier to parse in just a glance, but then it's no longer "just plaintext" in the same way that e.g. YAML isn't.
It probably works very well, but to me it looks a lot like a plaintext encoding of a database record or something. It's a different use case. Not a simple note that is "basically plaintext". For instance I would not feel entirely comfortable editing your example without worrying I'd mess up the structure or produce a syntax error. Though maybe the format is really forgiving, I can't tell. What happens if you forget the :END: bit, for instance?
With Markdown I can use any editor from a full-featured IDE all the way down to `cat` or `ed` and all I'm giving up are some quality of life features. It's the same format at the bottom, and it has the added benefit of being ubiquitous in that nearly every editor has some basic Markdown support. I can write it anywhere and take it anywhere, not so for Org-Mode.
I think I prefer the Markdown approach of keeping the file format light and plain, and building the quality of life features on top in the editor.