Ah, I fear doing quests because of all the problems. I am working on my 4th pirate, and she is almost 2 weeks old. I deleted 2, and am keeping my other old one. Since she is so bugged, I won't list her here.
Kelly O'Hara
Cutlass 7
Pistol 8
Cannon 17
Sailing 10
Notoriety 17
Quests
Working on dagger, need tongs. Have killed over 20 sergeants, no luck. But, don't mind because I know the next step, the big ship, isn't there yet.
Working on the Carver quest. Need 13 ships.
Teeth, Rings, valuables, etc.
The best place to find all of these, is in the swamps on Cuba. Yesterday, I found several items for all the categories.
The best way to level up sailing is to have a crew shoot while you stay at the helm. I you leave the helm, you won't get much for sailing.
See you all in the game!