The randomizations sounds very good for me. It would be interesting for a future campaign (Only if you plan it) being able to adding randomization to other ports.
I'd love to have for this mission some torpedo fail rate. Like dub, or those configured as impact that miss because their angle of impact is far from 90º. Magnetic/speed for vapor ones, would be nice too. In the 39 they should fail a lot, in the 42 they should be better (I hope see later dates! like 43 or 44 for those of us that like difficult games!).
Because if the torpedo is perfect you can fire it safely and in an accurate way (0 knots..., just aim the scope) at 4-5Km. And if one hit mean one ship, you may do your own "Pearl Harbor" with just your five preloaded shots.
Another idea would be adding more chaos once a torpedo hit or you get detected, like cars moving, people running to destroyers, SOS calls, (lifeboats in case of regular convoy games) - but I think it's too much work. Also, a good retreat if mandatory.
If you are able to surface the boat without being seen for some time + reach deep waters + sink at least one capital ship, then it should be a Victory. It should be pretty fun to see mad destroyers looking for you, and maybe randomnly deep charging to express their anger. Also planes in a future, looking for revenge.
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