This idea has been developed and deployed to Canvas
When students run into a broken link (e.g. link to file that has been deleted) they fill out the "oops!" error report, which is sent to me as a Canvas Administrator at our institution. I will then forward the error report to the course instructor. Wouldn't it be more helpful if there is a way for this type of error report to be sent immediately to the instructor?
I'm guessing there is metadata originated on the "oops!" page that would differentiate missing file errors from other types of error screens, so Canvas would know which type of error messages to send to instructors and admins vs. errors to send to admins only.
Perhaps there could be a prompt on the error screen asking the student if they ran into a broken link, and give them an option to message the instructor directly (an of course send this error message to the Canvas admin as well).
Bottom line - broken links to deleted files is not a system error. It's a user error, and thus it's more important for the instructor to know about it than a Canvas admin.