Just thinking out loud based on the allegation that pre and post roll advertising on Web videos won't fly. Wouldn't a Google class problem be, using organic metadata only, place new forms of advertising within the actual video? Automatically identify good cut points, come up with a new unobtrusive interface to alert viewers to sexy comm...er...potentially useful information, invent a few compatible, yet effective ad forms, and develop a new economy for contextual ad placement.
And of course, do it all at Web scale.
Think of it as AdSense for Web videos.
I'm not sayin', I'm just sayin'.