For me, a few of what already was mentioned:
corrupted save files, unexpected CTD and the micro-manage crew+fadigue.
Also unable to save a game near a ship/convoy, since it leas to the corrupted save files and of course a few things that tends to be historical inaccurately, plus the how the game AI reacts, since even during the happy times is hard to get very near a convoy at night.
Of course it is also a game and old one, and limited by various factors.
At least, super-mods+ several mods manage to get the game more realistic.
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