You know...

I'm willing to bet there are coves of anti-NeoConfederacy rebels in our universe's Florida coast that would be more than happy to resupply Cuban or Jamaican pirates for the right price. If someone were to make such a nation, I'd totally point them toward OOC collaboration with that player.

EDIT: And yeah, the trickle of trade is a very realistic thing, too. You might not see a Jamaican in Massachusetts, but sugar cane could worm its way up there.