2: Do you find that chest in any other ship which you board? Not your own - attack an enemy ship, fight your way to the cabin, duel the captain and then see if the chest is there. If it is, I can easily add it to the quest cabin. If it's not, assume you bring the chest with you when you take over a new ship for yourself. Likewise, a captured ship will have a ship's locker and a weapon chest containing random equipment, but only the ship's locker and weapon chest in your own cabin will contain whatever you put there, and they'll continue to contain your equipment when you take a new ship for yourself.