I agree. Sort of how xhtml never really caught on because it was too strict. I never understood the desire to make things break when it's often less effort to make them work.
Though I think the biggest benefit of JSON is that it is so simple, at least compared to XML. It makes it harder to just dump your internal data structures as is. Which forced people to actually serialize their data. Though with time people have overcomplicated it with objects that have "type" and "value" fields, basically designing their own standard.
* There's a lot of programmers who will send a string, or a null, or maybe a float, or maybe it's always an integer, and deeply don't understand why you care what it's getting serialized as.*
As far as changing the type depending on the situation, I kind of wish that was more common. I like the idea of conveying meaning based on type, but for it to work well it would need more standard types, plus anyone using a static language would be mad at you.