@crockett36
Exactly the question behind the question - why do it at all? What is the motivation?
Is it that once you reach a level of mastery that the outcome is garaunteed as to which power will win? Is it knowing that you won because of better play, or because of playing the side “destined” to win? Does playing the through twice, once as Allies and once as Axis, help determine who was better - did you win when you “should” have, and how soundly?
To your second point on handicaps - that’s how I always saw bidding - a comination of handicapping the game and/or one player. I think the question remains the same however - why do either (balancing or handicapping) in the first place? As a novice player, I’ve read references to “you’ll know the imbalances when you get that good.” However, if you know what those points are (the enemy advantage) then radically modifying your strategy to maximize what advantages you do have and counter the enemy’s advantage / exploit their weakness would be the sporting thing to do, no? Also to your point on historicity - this is how real commanders had to “rebalance” battles in their favor. In doing so, you force the other player to respond in kind.
I’m unsure of your third question’s intent, but will take a gander. I imagine everyone wants to win, but does doing so the same way (or loosing the same way) become stagnant? Per the second point above, I can also understand the desire to MOD games for new challenges and to add new dynanics into games without having to wait for commercial game developers to issue new kit. Perhaps that is similar to some video games that offer an arcade, normal, and historical/simulator playing options?
Thanks for indulging a bit in the thinking behind the scenes! Hope to hear more philosophies / motivations!