industrygothica
Adventurer
I wasn't saying the pirate HQ would be in Umbra's lands. They would be on the south shores of Island #2 (opposite side of the island from where it's marked Foghollow (that pathfinderq1 wants to rename Silverport). So the pirates are on a whole other island, but they prey on boat traffic between the 3 main islands. Count Umbra would be a villainous sort that hides his evil side in polite society and poo poo's the 'criminal scum' in public while secretly being part of both the Thieves Guild and the Pirates. Think of Count Dooku in the Star Wars prequels. Has most people totally fooled that he's an upstanding citizen while he enjoys slumming with the pirates in an alternate identity. His pirate ship, The Bloody Wake, would never sail into Heartbreak Cove and moor at his private docks. He want's to keep those two identities far apart as possible.
I think the pirates are a problem for everyone, not just Kingsport. But maybe they're too firmly entrenched for anything beyond a united effort by most major governments from all the islands to actually defeat. So they are dealt with piecemeal and various countries offer bounties or Letters of Marque to make interested ships officially sanctioned pirate hunters. With so much ocean around, I can't help but think naval travel and shipping have got to be huge. This would always invite naval based criminals (namely pirates) to prey on them unless they are chased out of an area or the government pays for heavy patrols. So the area close to Kingsport is probably heavily patroled, but nobody can project enough naval power to cover all the shipping lanes. Unless they send guard ships with every convoy, which gets expensive fast.
I can live with that. I need to open up a waterway on the other side of the Central Marches map, and I'll open up your Heartbreak Cove at the same time.
-IG