Yes, the game would be really boring if you were forced to repeat every mistake that was made in reality. On the other hand, if the factors which led to those decisions aren't included, and there's no incentive for taking the historical approach, then there's no reason to call it a historical game, rather than a generic sandbox wargame set in a pseudo-WWII timeframe.
To me, the ideal is to create the conditions which led to the historical situation, but allow one to make other choices with realistic consequences. Being able to change a few specifics here or there would have been historically possible, but changing one's form of government without major social upheavals, or refocusing the military in a totally new direction without problems (such as the chaotic mess that the Purge made of the Soviet army), would be unrealistic.
To me, the ideal is to create the conditions which led to the historical situation, but allow one to make other choices with realistic consequences. Being able to change a few specifics here or there would have been historically possible, but changing one's form of government without major social upheavals, or refocusing the military in a totally new direction without problems (such as the chaotic mess that the Purge made of the Soviet army), would be unrealistic.