First off - WOW! Thank you for such a wonderfully detailed response!

The willy-nilly appearance is kind of intentional. Originally, this island began as a loose collection of several disparate groups seeking refuge here during a war. They each built their own encampments which have in turn, over time, become individual settlements. Also, I have a whole mess more of buildings to come.

1) I like your idea about a rough grid near the docks. Which is in fact, where one of the major camps originated from. This island is massively populated. It is actually located at the center of a freshwater lake that is mildly geothermally active. It is pretty much the 'center of the world' for my campaign. I didn't really use any specific program to design the city - though I did use that generator to create several 'streets' (mainly because I was too lazy to draw all the squares). Though, to be honest, I have gotten away from that recently and gone back to hand drawn.

Thank you for the links BTW! Fogdown is one of my all time favorites, and in fact, I use it as a basis for another major city in my campaign.

2) Good point about the markets. I totally agree.

3) That area is in fact a temple mount. I have to keep it where it is due to events that have already taken place in the campaign. Though to be fair, when this is completed, that will be centrally located. The bulk of the island is all city.

4) Some of the buildings on the island do represent fortress like buildings - or at least they are supposed to. Since it is a freshwater lake that is surrounded on all sides by a single country - of which Opal Island is pretty much the capital - there has never really been the need in game for a wall.

5) I love the idea for a wharehouse district. Thank you! Now I just need to decide how I want it represented.

Thanks again for the tremendous amount of advice! I really appreciate it and more is very welcome! I will post my progress as it develops.