Need advice: Night Surface Attack for cowards.

[Platapus]

I started yet another career. 94% realism (still have to keep that fuel at unlimited). This is my first career with totally manual plotting and so far it has been a frustrating challenge, but that's what sims are supposed to be.

In the past, I have shunned night surface attacks because I am a craven coward (they don't call me the Joe Besser of Kaluens for nothing). But I would like to get into night surface attacks.

I play DiD for the most part so that makes me a little less heroic. There are old Kaluens, and bold Kaluens but very few old bold Kaluens.

Let's start out with a lone Merchant. In a Type VIIc, on a dark night clear with some moon, how close can you get before taking deck gun fire? Is it reasonable to get within 1,000 meters?

Once you have launched your torpedoes, what is a good way to turn in such a way to avoid being spotted. Approaching a ship bow-on leaves a small silhouette but once I turn won't they see me and try to hurt me?

Using GWX and OLC do you use the periscope for surface night attacks or is it mostly eyeballing it through the Uzo?

If there is an escort, do you shoot the escort first or is a surface night attack not recommended if there is an escort?

I usually don't mess with escorted convoys but I would like to learn some techniques for attacking, but much more importantly, surviving convoys.