So as well as the area map, I am also going to try working on the city map for the dnd game I am in now.

I have joined part way through, so the town/city has already grown somewhat and stands at a population of about 4,000.

The initial city started of with Oleg's Trading Post and has grown since then in a number of phases as follows (these are areas not solo buildings):

1. Olegs (Shop)
2. Housing and Smith
3. Temple to Tempus
4. Jail, Garrison, Monument
5. City Walls
6. Housing and Inn
7. Market and Housing
8. Library and Shrine to Oghma
9. Granary

Going to try and design the city to show the development in these phases rather than planned from the start