That top one really gets me. That employees in flight operations wouldn't understand the concept of dead reckoning is used in a flight tracker. Well not that some would have been confused... But that nobody in the room would have raised that over a several hours span.
Even on a pure UI level, any software used in such a role really ought to warn the user somehow for "this aircraft has been X hours out of contact" in a world where this isn't supposed to happen anymore.
You also figure it out pretty quickly when you watch a few plans make physically impossible jumps between their dead reckoning location and their actual location.
