At the start of every new career I do a quick trip around the harbor on August 1, 1939. When I'm done I set 'Days In Base' to 18, which makes my first "real" patrol start on the 19th, the day the first boats were sent into the Atlantic to await the start of the war. After that I reset it to Random.
As far as I'm aware that's the only way to get an exact start date. You'll have to start on May 1, 1941, then quit the patrol and set 'Days In Base' for 15. You end up with your first real patrol being listed as your second, but I don't know any other way to do it.
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“Never do anything you can't take back.”
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