1. So what if JSON is primarily used for data interchange? It's not like allowing comments would somehow make them magically show up on serialized objects. This objection makes 0 sense to me. And heck, tons of other serialization formats (e.g. XML) support comments. Besides, there is a big reason that human-readable serialization formats are so popular - because they're human readable! If you're really worried about size you should be using a binary format anyway.
2. "Rigid rulesets" has nothing to do with Crockford's arguments. It's one thing to prefer a particular type system, or limit functionality if you think it has high potential for misuse. By JSON not having comments all you end up with is worse workarounds, like putting comments in object keys.
3. "I'm not even sure why someone would want to write comments in package.json" To be blunt, then, I can't believe you've ever written any code in a business (i.e. with multiple developers) in the Node/NPM ecosystem. Is it really that hard to wonder why someone would want to comment why they added a particular dependency to their project? The lack of comments in package.json is one of the biggest complaints of this format, and it's certainly not just me, e.g. https://github.com/npm/npm/issues/4482 and https://stackoverflow.com/questions/14221579/how-do-i-add-co...