I also question the value and cost of syntactic sugar like chained comparison operators, negative indexes, even semantically significant whitespace/indentation.

I also question the value and cost of syntactic sugar like chained comparison operators, negative indexes, even semantically significant whitespace/indentation. They let the programmer take shortcuts, but unless they're always attentive of their implicit behavior, can be a source of subtle bugs. I say that as a one-time enthusiastic user of CoffeeScript, which felt so refreshing and elegant at first. Over time, especially working with other people's codebases, I came to a personal conclusion that it's not worth the convenience. Syntax sugar can hide logic that would be better explicit. Even if it feels verbose, there's value in being able to see exactly what's happening. An example of the latter that I've heard occasionally, is how error handling is done in Go. Every single function call that can return an error must be explicit handled (as far as I know). There could have been some sugar to make it simpler, but they preferred to keep it verbose. That was the right decision, in my opinion, and other aspects of the language give me the impression that it's a consistent design philosophy.