It sounds to me like you've learned that the game is nothing like real life, and you can "game" the game, do the impossible and ignore everything they had to deal with.
The 8.8cm deck gun had very little to do with the FLAK gun of the same calibre. That gun could elevate to very high angles, and shot a timed-fuse shell which was meant to be used in massed groups against large bomber formations. The chance of one gun hitting one aircraft was no better than, well, the chance of a u-boat doing it. More than 120 aircraft were shot down by u-boats. I can't find any that were hit by a deck gun.
Sneak into New York? Not likely. After Scapa Flow no major naval base was ever entered by a u-boat. I don't know of any being foolish enough to try.
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“Never do anything you can't take back.”
—Rocky Russo
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