> Ideally this diagram would be automatically generated using tooling... The biggest problem I've seen with architecture diagrams is they fall out of sync with the code base. In my opinion, automatic generation of these diagrams is necessary. Otherwise, teams have no way to know whether the picture in front of them accurately represents the latest state of the system.
I think the best way to document a system is to write doco and just specifyc the intent of the system. What was this thing meant to do. That context is really useful for contrasting with the use of the system in a prod environment.