It is quite possible to launch a night surface attack early in the war, but I wouldn't recommend it against convoys, no matter what year.
One of the things that made such attacks so successful early on was the tendency of escorts to look for subs outside the convoy. Coupled with the near-invisibility of the U-boat, and the lack of radar, the chances of detection were very small.
But, as far as I know, in GWX, escorts don't turn away from the convoy and begin sweeping. They make a beeline for the general area of the attack. They also have searchlights, and have the benefit of being made instantly aware of your presence, and exact location, no matter who detects you.
Finally, a critical element of the surfaced U-boat's strategy was using its' superior speed to outrun many escorts. IRL, this worked out well on many occasions. Even when detected, the U-boat was all but impossible to hit with naval ordinance, and many of the ad-hoc "escorts" being used at the time couldn't keep up. Escort captains had to remain close to the convoy as well, to guard against further attacks by other boats. They were not at liberty to spend 6 hours chasing a U-boat, and their primary goal was simply to force the U-boat down and hold it there until the convoy had gotten away. Oftentimes, only one escort could be spared for this task, as the rest were needed for the convoy.
GWX, as fantastic as it is, does not model the world like this. I imagine it would be tremendously dificult, if not impossible, to realistically impliment a tactical doctrine that reflected that of the escorts' real-life counterparts. It is also limited by the stock SH3 programming in many ways.
The result is that, should you use a night surface attack, you will likely be gang-raped by every single escort and hounded for however long it takes you to prevent them from locating you for a solid 30-minute block of time. They will fire on you, and hit you a lot, and every single one of them is faster than you.
So.....no, I wouldn't recommend it, myself. But, I'm sure that there are more knowledgeable persons here who may have different opinions.
Happy Hunting!
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