I totally agree that in the ideal world, JSON should support comments. I yearn for them, and none of the in-band work-arounds or post-processing tools are acceptable substitutes.
But to play the devil's advocate, how would JSON be able to support round-tripping comments like XML can, since are part of the DOM model that you can read and write, while JSON // and /* comments */ are invisible to JavaScript programs. There's nowhere to store the comments in the JSON object model, which you would need to be able to write them back out later!
On important feature of JSON is being able to read and write JSON files with full fidelity and not lose any information like comments. XML can do that, but JSON can't. To fix that you'd have to go back and redesign (and vastly complicate) fundamental JavaScript objects and arrays and values, to be as complex and byzantine as the DOM API.
The less-than-ideal situation we're in isn't JSON's fault or JavaScript's fault, because JSON is just a post-hoc formalization of something that was designed for a different purpose. But JSON is rightly more popular than XML, because it's extremely simple, and nicely impedance matched with many popular languages.
YAML suffers from the same problem as JSON that it can't round-trip comments like XML can, but it fails to be as simple as JSON, is almost as complex as XML, and doesn't even map directly to many popular languages (as the article points out, you can't use a list as a dict key in Python, PHP, JavaScript, or Go, etc).
You can sidestep some of JSON's problems by representing JSON as outlines and tables in spreadsheets, without any need for syntax and sigils like brackets, braces, commas, no commas, quoting, escaping, tabs, spaces, etc, but in a way that supports rich formatted comments and content (you can even paste pictures and live charts into most spreadsheets if you like), and even dynamic transformations with spreadsheet expressions and JavaScript.
See my comments about that in this and another article:
https://news.ycombinator.com/item?id=17360071
https://news.ycombinator.com/item?id=17309132