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I'm not so sure about England... but it could work. The main reason being that we are pirates and the British Royal Navy is prowling around these waters, and hates our guts haha. Although perhaps it could be done. I don't really see very much wrong with it.
I say yes. I don't see why we shouldn't have one or two more SvS islands to play for. The more teams, the better. The only problem I forsee is that there will be more space for SvSers, so it may lag badly in the area where most ships will do battle, but that isn't too bad. Perhaps they could add two new SvS islands, but in a different part of the Caribbean, so the SvS ships aren't all clustered in one area.
Some ideas that could be used for factions could be British or Dutch, like you said. They could mayble also use Portuguese, as they were a power in those days. Perhaps they could even consider an Arabian nation or an Asian one (Singapore, maybe? They weren't a huge power though, as far as I know.)
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