Can someone share even one story where sudo reporting these "incidents" was helpful? This feature seems to come from a world where elite hackers simply repeat the same sudo command over and over hoping it will eventually work.
Yes. More or less the first time I used Linux was on a fedora workstation at my desk at MIT. The very nice sysadmin down the hall sent me an email just a bit later saying "We see you were trying to install x program. We installed it for you." I understand that this is a very rare experience but the first time I saw that message, a helpful person was actually looking at these reports.
I cannot really imagine that happening today, at least not in "professional" context.