Thanks for the feedback @spajus. It’s always good if we can find specific tasks to improve the experience for users and administrators. Generalising things in one large topic makes it difficult to turn them into actionable tasks.
Looking specifically at your second bullet point. We aim for discourse_docker to be compatible with the latest stable. Are you seeing something different?
As far as I know, this should be resolved and is no longer being investigated. If it’s still broken, let us know. The sed fix is a bad idea, as it will probably break more things in future.
If chef is only provisioning an OS, and you are using discourse_docker, then it does seem unlikely that chef is causing the issues.