It started when a lot of us complained about starting out on the first day of the war and trying to run at full speed through the Channel before September 3, when the enemy started blockading it. In real life 14 u-boats were sent to the North Atlantic on August 19. Since the game won't let you start a career on any day but the first of the month, it was either stay with September 1 or go for August 1.
So that's the point of starting in August.
Of course you can always start in September if you like. Or January 1940.
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“Never do anything you can't take back.”
—Rocky Russo
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