What would a city built by pirates look like? The decorations would be haphazard, because it's all from loot. Your loot might not have enough angels' statues to decorate the entire building, so you'll have angels next to gargoyles. That's the opinion of Rob Rogers, who explored the concept of a pirate town in his novel "Devil's Cape". Stuff like that is discussed on perennial panels on world building -- a crucial part of every science fiction or fantasy novelist's job. Maybe because it wouldn't be right to just reuse panel titles from last year, this year's panel was focused on City Building ("Creating a city that both works for your story, and makes sense for the world it is in.") There was the usual advice on the importance of consistency in city building, like in all world building if you want to have 10000 monkeys in the story, start with that city that could support 10000 monkeys. Don't just put it in as an afterthought in the middle of an agrarian country, or you may discover that it will support at most 8000 monkeys! (Scott Lynch).
Scott Lynch, Jayme Lynn Blaschke, Rob Rogers, and Vincent Docherty in the City Building panel.
Scott Lynch also suggests that if you want to get a handle on realistic city-building, try to develop an interest in solid waste management. Combing through other people's waste used to be a major part of people's pastime in medieval and even early industrial times. Masses of poor people would wade in the sewers, capturing lumps of waste, and picking out anything that was remotely valuable, discarded by upper classes. In Victorian England cities, that had long outgrown their medieval infrastructure, there were thousands of people involved in the business of transporting other people's "nightsoil". All this was a subject of Steven Johnson's book "The Ghost Map: The Story of London's Most Terrifying Epidemic--and How It Changed Science, Cities, and the Modern World", that Scott Lynch got his wife for Christmas. That's the kind of guy he is! :-) (In his defense, he said his wife is a biology major, and fascinated by pathogens.) Even if you are not into pathogens, stuff like this surely helps a fantasy writer to create a realistic medieval world.
Pictures from ArmadilloCon 2009 are in my photo gallery.