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The extra content for Helen is you can play sandbox as Helen and when she captures the Pink from the Black Mark DLC she has extra dialogue and gets a special achievement. She also starts in sandbox using the war schooner Rainbow which was mentioned during the Pirate Saga and there's another achievement for fully upgrading it.
Some people pick Mary because they pity her. As you said, Helen owns a whole island, while Mary lives in a small, disgusting cabin of a rotting ship. Given the opportunity, shouldn't you rescue her from the horrible place that is 'Justice' Island?
I still prefer Helen though.
v1.3 introduced new scenes for both girls in Longway's quest.
Helen has a whole quest whilst Mary is tied to the Justice Island quests.
Mary as a girlfriend is a brilliant fighting officer.
Helen provides you with a full ship upgrade that costs thousands of doubloons, but you don't need to provide any strategic goods. She can also start off with 90 navigation, 75 accuracy and cannons which is pretty valuable unless you have been spending too much time on freeplay and have officers that are better.
Since I play story mode on the highest difficulty, I pick Helen because XP gain is so slow.
Also Mary is the best Vanguard in the game.
Wrong. Nothing lasts forever.
Helen's name is just being used for the Brethren to continue their ownership of the island.
If you pick Helen, nothing special happens, but if you pick Mary over Helen (meaning you still have to fulfill the prophecy), Helen will stand in the residential room and will stare at you and Mary as you walk around.
But in any case, I would always just pick who feels right for me (not Charles, me).
In order to romance Mary all one has to do is to love her and not to cheat on her. And save her life like a gallant hero. You get a lovey dovey kickass vanguard who will NOT let Charless get cold at night. Plus you won't look like a gold digger and Jessica will bless this relationship:)
In order to romance Helen one needs to suck up to her like a natural simp, as doing any less than perfectly reading her mind and fulfilling her every wish immediately ends the relationship. And even a successful relationship is borderline sexless as Helen will blueball Charles quite often. :P