All said and done, I still would love to play a genre-savvy dramedy game of real-world people playing an MMO or fantasy game and having the scenes 'flip' between the two as required.
In practice, it would be funny to allow a PC to use an inspiration or Fate point or the like to save his PC by strategically flipping the scene at a key moment.
"The Ogre stomps his foot, knocking you down. As he raises his battle-ax to swipe..."
[Player spends his Fate point or w/e; now the scene is real-life around the table]
"Woah woah. Where did the Ogre get a battle-ax? That's not part of its standard gear."
The most successful game I ever ran that had someone mundane find themselves in DnD was years back when a buddy of mine, who was a HUGE WWF (Not WWE mind you) fan created The Ultimate Warrior. He spend hours coming up with how the various wrestling moves could be converted to actual unarmed/grappling attacks. He also researched everything he could about the actor (athlete?) that played "the Ultimate Warrior" IRL. As I recal he eventually bought the farm fighting a Bulette...