Devlin M. said: @Gold, ... I guess I just needs to learn to work from the top down instead of starting at the points of interest and working outwards. Thanks! Yes. There are some tips and techniques that can help. First is just planning your districts -- you did that -- and some subtle background colors, floor or textures, you did that. You can then overpaint large blobs for neighborhoods (it will later be covered up with detail and becomes just a part of the ground color). Secondly, plan the rest using plain squares for the buildings and delete them after planning; you would not need to place-map-features from the top down if it was an overhead map (non perspective). So you could plan / pre-draw your city as an overhead view just to get the arrangement of important building locations and work out from points of interest. Once you've made note, delete and over-draw with the Russ buildings now working from top-down so they stack nicely but following your plans. Granted there are some limitations of using Old World Styles to attempt to precisely recreate a plan of streets and grids, the town buildings in this are best-suited for 2 angles (regular way & Flip Horizontal way). They tend to form streets that X across the map, rather than cardinal directions. So these are best used for neighborhood density (in the way you used them) and also for Symbolic (where 1 building isn't = 1 building, but instead means something like "small village here"). I agree with Russ that you got the nice feeling of streets in your map, without drawing streets, just the gaps between buildings, and the sections that are almost too dense to pass through are intentionally impassable. If you're still editing, I would say you could make that stalactite temple on the left, even larger. Make it looming, because that would look cool, unless it's too outrageous for your setting. @ Russ "those towers" have been used for several places in my game... off the top of my head they have been a Church steeple, a Magic tower, a Knight's keep, the Ruins of an old keep, and stations along a city wall. One time a major magic artifact was stolen from that token when it was a church steeple (had a magic bell). Another time the party spent the night in the Ruins crumbling version of that turret and got ambushed by orcs inside & outside it, an assassin snuck in through the window. Another time the Dawn Priest got turned to stone in an underground dungeon and they took him as a statue to the top of one of those towers & let the morning sun hit him which turned him back to life.