Yup, it's such a small thing, but it actually makes a huge difference. C++ has the same problem when dealing with optionals, etc. etc.
(I know absolutely nothing about Dart, but it does sound a bit weird that the expression-ness of an if is contextual. Is there a good underlying reason for the exceptionalism here?)
Dart also has spread operators and for-expressions to make writing "UI with code" much easier. It's fresh to see how language design choices are being made more by pragmatic ones (for Dart it's the fact that it's primarily being used for Flutter to make UIs) instead of ideological ones (One might claim that "if" should be a pure expression following the tradition from functional languages like ML, but that also has its own set of problems in a language designer's perspective)
https://medium.com/dartlang/making-dart-a-better-language-fo...