Southport

The City-States Region tends towards being insular, with most residents wanting nothing more than to live their lives in their town or city, and without giving a second thought to what might exist in the wider world. Even most merchants are content to manage a small slice of trade between cities, whether shipping iron from Aratosa or bringing food out of the Fertile Lands down the Lasair Canal. 

A small number of traders get the desire to seek their fortune much further afield. Of these, a large percentage travel to the south, where it is possible to acquire rare goods from relatively foreign lands. As overland travel from the City-States to The Southlands is largely impossible due to the Shifting Jungle, trade from the south must traverse the dangerous waters of the gulf off the coast. The ships that make this journey will find their safest landing point to be the town of Southport, which has grown up at the mouth of a river.
From here, trade runs overland across the Southern Wastes, reaching both Mina'Satie Bay and the Korth'an Conclave. That trade requires guarding, thanks to the Minotaurs of the Horned Peaks (as well as other more varied threats). 
Southport has grown to support all of this. It boasts a small community of adventurers and former Mercenary Guild soldiers, ready to be hired for escort duty. It features many shops with supplies for both overland and sea travel. A handful of farms lay along the river, growing food for the town and for those traveling through. It is very much a town on the frontier, out of the safety provided by the Lasair Compact and the Mages, but that is just the way that those who choose to live this far to the south like it.

Rough and Tumble Town

When residents of the north hear of Southport (which is a rare occurrence) it's often with the air of "that dangerous dirt hole" where "you'll get your purse or your throat cut". Its reputation is of a place where you must always be on your guard, and if you look at somebody wrong you'll end up facing down a dagger in an alley. In truth, Southport is not anywhere near as violent and rough as outsiders make it seem, but it is a place that operates on its own set of rules.  Many of those who operate in Southport are very protective of their business. By actively choosing to leave the Guilds of the City-States behind, they abandon a system by which anybody with suitable skills can find work with those skills. Instead, the various merchants and tradespeople of Southport operate in a far more cutthroat matter - though rarely is that phrase taken quite so literally. 
The town has created its own culture, where outsiders must prove themselves and are distrusted to a high degree. Those who have set up shop and survived are respected, while those who come into town with high expectations are given a cold shoulder until they show they are capable of being useful without stepping on the toes of anybody else. 
This even extends into the community of sellswords that make their base in the town. Guard duty for a trade run into the Wastes, while dangerous, is extremely lucrative. A regular position with a trader's company is valued jealously, and a guard will be fiercely possessive of that role. More than one new arrival has been called out for a fight in the street over offering their services to a merchant who already had a working relationship in place. And more than one merchant has had to suddenly seek out a new guard after their "usual guy" met an untimely end.

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