Description of the need
When a user creates a date field for a content type, they choose the date format that they would like to use. Then they add a date to a node and notice that it is displayed using a completely different format.
While this is expected behavior. The display format is currently set in the display mode, this feels very counter intuitive to me. I would expect that when I create a date field and set the format that the format would carry over to the display.
I select this as the date entry format on the field

Then I create a node and see that this is the output.

Proposed solution
When a user sets the default input format for a date field the default display format is set to match the input format.
Alternatives that have been considered
The current expectation that users will configure the input format and the display format separately is not unreasonable. I just think it's confusing for new users and that if we could create a better default behavior it would be easier for new users.
I believe that most new users are thinking about the display format when they configure the field and don't necessarily have a reason to format the input value differently from the display value. For those that do have this need, their process will pretty much remain unchanged.
I am concerned that this MIGHT be more work that it's worth and that it might open a can of worms, in terms of other date formate related assumptions that we are making. Maybe it's easier to leave this as it is.
Recent comments
I use Lando (a wrapper for docker) and find settings changes happen straight away
How often is the settings.php loaded.
You might need to add a Relationship in the View to Flags. Or there might be a setting on the content type. I can't recall for certain but I think it's possible.
No Flag fields in Views
Try using caching in the View settings, set to 24 hours. This should work for anonymous site visitors.
View to show a different node each day