3 approaches to organize an ever-changing calendar and complex schedule

Interaction workers see ~50 hours per month spent on reading and answering email (on average ~109 emails per day) – and a large part of that time is invested into an email ping pong to organize an ever-changing calendar and complex schedule.
It seems to me that we could create 3 segments for the solutions the market ended up providing to the pain of scheduling meetings.

  • You
  • Virtual Assistant
  • Personal Assistant

The vast majority of us surprisingly choose  to take on the scheduling pain ourselves, even when it is obvious that it is financially unsound! I do however see that some of us try to aid the human process through the use of productivity software, but sadly not to the extent where I see software as a segment on its own. I believe two primary factors are in play; a) we underestimate the pain for every single ping pong engagement we start and b) we believe that only we have all the context needed to conduct the dialogue.
Virtual Assistant
It very much seems like the interaction workers who turn to outsourced virtual assistants are the ones who are on the verge of email bankruptcy, but not organizationally at a level where they can go hire an in-house personal assistant – a luxury only a few can apply. The primary challenge which I hear echoed over and over again, is the one of continuous training, but unfortunately a forever missing context.
NOTE: We should not confuse this segment with Siri, Google Now and similar mobile assistants, which certainly provide a lot of exciting features; holding a human or human-like dialogue with another person over email while trying to resolve the initial meeting request is not one of them.
Personal Assistant
It is quite fascinating to a software guy like me, that the best solution so far, to that of managing your schedule, is a human personal assistant! It also seems like the primary value they bring is a lot of contextually solid brute force. You simply ask Amy, your assistant, to go figure out which day, time, location and potential duration is needed for a meeting request. She can do all the email ping pongs she wants, as long as you are not involved. Shifting the pain from the interaction worker to the personal assistant.