We built a custom theme with hints for this sort of thing. It's put a dismiss-able alert at the top of the page if we see anything that commonly causes support issues. Even basic things like "do you know your course is hidden", "this course had no enrolments", "this activity has permission changes". The theme is too specific to be shared but it isn't that hard to do and might give someone some ideas.
Comparisons and advocacy
Canvas vs. Moodle
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