I thought it best to sketch out the town layout including walls/hedges, trees and the cobblestone road. I settled on five sections laid out in a cross pattern. Once I had a rough idea, I started on the nine remaining buildings.
I roughed out all the buildings like this one before going onto the windows, doors and roof.
Once I have all the buildings to this stage, I'll get out my spackle for the sides of the building and to cover up any mistakes.
Almost done with all the buildings, I start getting "crafty" at this point to make each building unique. I'll do more walls as well and then start on a few simple hedges.
It kind of gets messy but I like to wait before tossing the scraps, as I almost always need some of it to fix mistakes.
I keep a base on hand to test the height's and make sure they do not dwarf my "tall" 20mm buildings.
Here is an example of a "crafty" building, I was just going to have a short and tall rowhouse building next to each other. Then decided to turn it into a gate house next to a building. I have only attached it to the smaller building as I think I can also use it next to a wall section for a gate. This way I can have it face to the outside or the inside of the village/town.
I'll update the status of the project once I start spackling the buildings.