Merchants can safely be sunk by deck gun as long as you know where their guns are. If their gun is on the stern, approach from directly on the bow and vice versa.
If it's a Liberty Ship, forget it - they're like floating fortresses!
Best merchant moment? I came across a convoy of three merchants escorted by a single Black Swan. Sunk the Swan with a head on torpedo then surfaced to take on the merchants. Found out they were all armed when I surfaced, but the forward two ships only took 1 or 2 rounds to sink. It was only later that I worked out the rear ships were firing at the front ships while trying to get me, greatly reducing their hull integrity and I was lucky enough to fire the coup de grace on each of them and got credit for all three.
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