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I like the idea of maybe switching to/keeping the other ship, but IMO such a venture should 'scuttle' the ship being left behind. You beat a flagship and the question comes up "Acquire ship?" and if we say yes, we all move over to the new ship, and watch our old one visit davy jones (this would be somewhat accurate). Obtaining extra ships for selling would not be very accurate, plus you cant sail 2 ships back to port.
Real pirates would often switch ships when they took one over. They seldom 'kept' the ship they were leaving when doing so. Very very FEW pirates ever had more than one ship. Only a few renowned pirates actually had more than one (or a fleet) of ships at thier disposal.
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