If you were to log in, you'd be able to get more information on your fellow community member.
It's a good idea, but I think it's overly complicated and intrusive. While not all of the problems could be eliminated without this level of connectivity, some could. First, an initial pre-flight planning phase could be solved by a dispatch-like service that would take into account pilot experience and flying frequency (either initially provided or built from history of use,) and other things like equipment capability. It would be both a convenience and a safety resource, although the liability aspect would have to addressed somehow. Then, a lot of the stupid-pilot-tricks components could be solved by cockpit integration. The ERJ145 balks at you when you're not in the right configuration for the specific phase of flight. This is not a difficult system to include in GA aircraft, it just requires a bit more integration. This could take care of the flap/gear/trim/fuel etc. issues. I personally would prefer these choices to video-chatting in the cockpit with some guy I don't know, ...