Experience with the X-Wing Miniatures Game provides a lesson for the Python community. We need to find a way to strip things back so it is easier (again) for beginners to learn the language.
Python is used by very different groups of people and how we decide which features are Common Python and which are Situational Python must take that into account. If something is common to one group only e.g. data scientists, or enterpise web application developers, it should be considered Situational Python - even if the use case is very common for that group.
Python prides itself on having one obvious way to do things but it is more of an ideal than a reality sometimes. But we should still aim in that direction.
The When of Python is a fledgling community initiative. The goal is to effectively shrink Python so it fits our brains by providing guidance on when we should use particular language features (and when we should not).