The really good dynamic campaigns make it possible to lose a battle that was historically won. Imagine the fate of Stalingrad depending on your career of successes and failures, that would be something! A lot more pucker factor than just having to complete a mission in order to proceed.
Good lord, what a horrible idea! Determine the winner or loser of historical battles via some convoluted mechanism based on player performance (in the air forces to boot) is about as believable and realistic as expecting a straight answer from a politician. That is the greatest sin a campaign system can commit in my book. Dynamic in the campaign sense should be limited to what is realistic and possible - which essentially means the type of missions generated. For example if your Stuka Staffel is supposed to wipe out a russian artillery position but fumbles the first mission you're going to go at it again until it's done. Otherwise history should be both yardstick to measure accuracy and timeline for specific events since nothing a single player does can change the course of events so much that history is altered to a noticable degree.