How do you keep your documentation up to date?
What do you use for automating documentation and architecture diagrams, and how come?
I would love to know more about what you struggle with and how you tackle these thing where you work.
Disclosure: I'm the CTO of hava.io and we are trying to solve automating architecture diagrams
That isn't exactly the answer to your question, but I believe it is a very good idea to live by.
As for my personal experience, we just ping a Slack channel whenever an article is old and has to be renewed. But we also don't have a very big company, which means not a lot of documentation articles to monitor.
I.E. A code/solution review must also consider the documentation alongside the feature or solution.
This implies that the documentation is (held beside) source code too and can be diffed/compared e.g. Markdown for text, mermaid/graphviz for diagrams and that this can be built, rendered or published easily/readily (Hugo, zola, etc)
Definitely want to use your product in the future.