Maybe you're playing it on a different difficultly level Robins, but I seem to do okay in surface battles a lot of times. I can often outgun subchasers (I did when I snuck into Tokyo Harbor. Two 40mm and a 4 cal bow gun can make short work of it, surprisingly). Medium Gunboats are also pretty easy to take down with the deck guns.
If it's night time and you think conditions are better than normal, go for it and surface (after saving your game, just in case). I would say that you can probably go in a near head-to-head fight with a Mutsuki or Minekaze, since your sillouhette is much lower, you're pretty fast, dark, and your single gun is better than one of their single guns.
Anything bigger than that is suicide. MAYBE, if you are VERY lucky, you could fight a Shiratzuyu. But even the Shir has great surface firepower; once in an S18 I was forced to surface, three destroyers just made the air thick with gunfire. I really was getting hit about twice a second.
So bottom line: Avoid tangling with these boys. If you can outgun them without damage, go ahead (not probable.). If you can hit them with a torpedo, do it and cripple/sink them while you work on the convoy itself. If none of these work...avoid them entirely and sneak through. If you can't, then just distract them with flank speed, while you sneak into the convoy (though this does set them on alert for pings then).
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