I think that this can only be judged by experience, you as a SH3 player get to know your skills and weaknesses, for me personally, it is convoys.
I like to get in nice and close, which will not work submerged, so by the time i'm say 7km from my targets, i'm around 2km from an escort. This has seen a few hairy moments and something I have to consider now.
The time that the game really tests you is when you have flooding and damage, and you are being DC'ed. For me, that is what makes the game.
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