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The DLC does have a few heavy item requiring quests. Here is a 'shopping list' I found on the forum. Just make sure that you have these items and the 'raise the Spanish Flag' ability and you are good to go.
I
Create a save before returning to Tyrex from the 1st misson and keep it untill you get to 7th mission.
II
Items required :
1st mission - 250 doubloons; ability to lift spanish or dutch banner; no bounty on player's head from spain.
2nd - 50 doubloons; 1 unit of shipsilk (you'll be given one); 1 long boat.
3rd - 50 slaves; 500 units of coffee, vanilla or copra; 30 weapons (goods from your ship); about 90 healing potions (+40 hp). Not essential - 30 soldier pistols with 30 lead balls and gunpowder; 2 muskets with 20 lead balls and gunpowder for each.
4th - no required items.
5th - 1 (any) spyglass and ship compass; 1-4 mirrors, jade rings or jade beads; 12 antidotes or more (get some for your hero and boarders, rum & mixtures will work too); 1 more (any) spyglass; 1 duelling pistol with 30 lead balls and gunpowder, 1 trombone with 30 grapeshot and gunpowder; 1 emerald beads; 1 ruby band; 10 unit of leather; 20 units of planks; 1 ship jointer, alive.
6th - no required items.
7th - no required items.
8th - ship(s) you can spare, you'll have to sink them.
9th - no required items.
10th - 200 doubloons; 1 flintstone; 300 units of gunpowder (goods from ship).
III
Some of those items can be found during the questline.
IV
Spanish & dutch will hate your guts, don't want hordes of bounty hunters on your♥♥♥♥♥- improve your relations with spain and holland beforehand.