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Skull and Shackles / Serpent's Skull crossover? (GM only)

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Do to player hijinks, I may have to consider a crossover. Is this discussed? And any opinions?
Silver Crusade
Pathfinder Adventure Path Subscriber

I'm already dropping Pezock and the Dryad on Bonewrack Island. The danger is that if you take all of Souls of Smuggler's Shiv into book 1, the island exploration gets in the way of the sailing and pirating, also the 4th book may repeat those themes so there's that.
Dark Archive

My current Skull and Shackles group is playing the offspring of their characters from Serpent Skull, so I'd consider what I'm running to be a sequel of sorts.
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