First of all welcome glad to see you surface
I doubt Im a 'better' player than any other here but I'll take a stab at these.
1.) Personally I ignore the escorts and go for the meat of the convoy. Some will say "Take out the escorts then sink the entire convoy". But to me thats a bit unrealistic. As far as going deep at flank while reloading... well uhhh.. good luck with that. Any escort worth its salt will find you easly and give you a good pounding. Also trying to keep up with a task force, even at flank, would be a neat trick, running at flank while submerged will suck your batteries dry faster than you would think. About the only time i am able to pull off a repeat attack is on a dark night where I can slink off surface and cruise ahead into position again.
2.) 90% of my torps are fired at Fast, Shallow, with impact triggers. I do try other methods but as I already said Ive had the most success with the previously mentioned settings. I try to aim slightly astern of the stacks where the fuel bunkers are usually located. Seems to be a weak spot. Furthermore I never fire a single eel, just in case one of them is a dud. High value targets may get as many as 3 or 4.
3.) Yes its a bug, game treats it as two engines for whatever reason. Used to be that you could get back with no diesels and limited batteries. There was a 'magical' solar charger. The batteries would recharge while surfaced wether or not your engines were running. Not any more.
4.) Dive planes... another known bug. The planes have no effect on diving performance and are just cosmetic. Try saving the game WHILE SURFACED reload and it should be fixed.
5.) The medals improve your crews performance in subtle ways. But basically they dont tire as quickly and things like load torpedoes slightly faster etc. BTW the medals are kind of random and hold no historical value whatsoever. I use them to 'reward' the members whom did the lions share of the work on a particular patrol. Wounded, Good gun work, Good torpedoe attacks, that kind of stuff. Its mostly role playing to be honest.
Anyhow again welcome and have fun. Dont be afraid to ask