Description of the need
If a Layout made its contexts available to its custom blocks, this would allow people to use tokens related to the entities in the context. Use case: create a custom block that displays some node properties like the created date, which are otherwise not selectively available.
Currently the layout contexts are not available to BlockText, which is the class that custom blocks use. While BlockText::getContent() does invoke token_replace() it does so without any context, meaning that only global tokens are fulfilled.
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