We always went to an Outpost whenever we had 1 Whining Chest (I guess its the Chest of sorrows) so the annoying Water stops, or when we had like 3-6 chests because it only makes it more rewarding to enemies if we would lose a battle.
We also never made a fight if we knew it wont be just a quick 1-3 Cannon shots and then sail away or if we had chests on board.
Also if we get a single Captains Chest, we always sailed immeadiatly to the next outpost to sell it for profit.

