I'm creating examples of each of the environments where my RPG takes place. For starters I need an initial town of a fair size, suitable to blueprint gameplay for any town / city. It needs to connect to each of the other environments: A river, a lake, a thruway road, a bit of forest, mountain-pass paths and an underworld dungeon or two. Enough for a vertical slice of the core systems of the game.
watabou's Medieval Fantasy City Generator is a great tool for making the base layout. I use this generator often in my D&D campaign already, which relates because it's set in the same world. The town won't end up exactly like this, but it has the features I need as a foundation.

(watabou's city generator is amazing!)
Just now I tried using watabou's sibling tool, a 3D city viewer that imports .json files from the city generator. Useful for basic layout, but it exports a single-mesh .obj that I found awkward to work with in Blender. Even for a bit of grey-boxing and to go any further: I'm going to recreate each building from scratch.
One big change from the map: I'm going to add tiers of height changes. That will make it more interesting, but also needed for the river flow. The way my river-shader works, I need height and angle changes broken into segments of breakwaters & waterfalls. The whole town changes accordingly. I've marked up the map to show the different tiers. Each number represents a layer of elevation.

(5 represents the highest of the town's elevation and 1 the lowest. The lake would be zero, relatively)
Now I need to get cracking within Blender, first with the greybox to get the scale right, then multiple passes of detail until I'm at least happy to walk through this town as a character.