I spent some time playing about with the Discourse docker manager and they’ve made it so that it only updates discourse instead of the docker base image, with almost no downtime.
With that in mind, I’m proposing that we allow the instance owners to update Discourse through the admin panel whenever they want, so they have the latest, and then we schedule a regular rebuild once a month to update the base image (with exceptions for security updates and urgent plugin additions). This way we don’t have to worry about scheduling maintenance and then lagging behind on updates.
If nobody has any objections within a week, I’ll update the wiki and pick a date for regular maintenance.