Oten'jo seems like a good opportunity to try making a city map, so here are my thoughts.
The more stuff I looked at, the more I decided that I ought to work out the skirmish-scale stuff first, like the specific details of the buildings. I've done a lot of this, so it seems like a good starting point.
Once I figured out how the individual houses relate, I began figuring out how big I could make each one on the map. This will determine the level of detail and I'm really hoping I can work detailed roofs and trees (at least, detailed to the point of my sketches) into the map.
Here are some of my sketches, mostly skirmish & neighborhood scale: