When we're trying to balance a trade off, I often wish we could just do A/B testing on it, but that's not realistic for languages.
The HTML5 spec was developed in this way, and some of the code-health folks at Google were just starting to operate this way when I left, but I haven't heard of many other language-design efforts working like this. The technology & data exists now, with large public corpora of open-source code, parsing libraries that can identify patterns in it, and big-data tools to run these compiler tools over a large corpus. It's a bit of a paradigm shift from how languages are typically developed, though.
https://github.com/golang/proposal/blob/master/design/12914-...