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If your pirate already has a song or loot, it can't get it again. So - transfer loots as soon as you get them, so you don't lose a needed loot because you got a bad one you can't transfer. You can give your doubles to one of your other pirates. At first I was deleting new low pirates to make room for fifth loots. Then I discovered if you let your "crew" fight a battle for you with a big ship, you can lose, and hence lose all your loot, getting rid of the bad loot that won't transfer over. I'm assuming if you sink in any way, you'll lose what loot you have, and thereby get rid of the rotten loot you don't need. Also I -think- at some point a new loot will jettison an old loot. I'm not sure how this works but it did happen to me once.
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