So one of the things that I love and hate about drawing maps is that they are incredibly complicated, and you really have to know what you're doing or you wind up with a lot of trial-and-error processes.
I don't know what I'm doing when I make maps.
With that said, I've finally gotten a start on working on the map of Yesov in Inkscape, but I wanted to run a few questions by people.
The way I'm setting this up is that there's sort of an old city and a modern city side-by-side. West of the river is this medieval village, and some 1800's era construction. East of the river is a modern city, with some interesting features. The northmost part of the city held a prison during the Soviet regime in Segira (this is the little black box north of the buildings), which is now serving as the Free Reds' base of operations.
The castle in the bottom left is their actual command center, however, and one of Petrović's missions is actually to put a land-mine on the road reading up to it in order to destroy the Free Reds' command/logistical vehicles or, if the players are lucky, the BTR that the Free Reds have.
The cropping I've reduced the map to more or less represents the majority of the space I intend to fill. On the right side of the city, everything north of the major artery that's already drawn heading out to the east will have more or less a grid layout, though distorted by the natural flow of the river just a little (this distortion will lessen, but the city doesn't quite extend to the edge of the map.
South of that highway across the river, there's not a whole lot. The foothils make it hard to build anything large, and if I can figure out a good way I might even draw something to indicate that this is rough/forested terrain. An enterprising group could use this to make a surprise attack.
I'm thinking about doing a green/blue/brown/gray setup for the map, with brown indicating buildings, light green indicating open land, dark green for forest, blue for river, and gray for impassable mountains. This has the downside of only really working well in color, but the upside of being far superior from a visibility perspective.
In any case, you can see some prototype buildings. The way that I made these is adding additional dividing lines in Inkscape, then using the paint-bucket tool. There's not much detail, but you can add to the experience by having some particularly large or small buildings, and some of the buildings get a distinct shape by having some of the dividing lines go places unexpected (the large building in the right of the middle row actually has an indentation in it, from a line that juts across the street. In high-resolution, I think this will add a nice little detail.
This is a little more consistent and predictable than anything computer-generated (not to mention probably easier, to a certain limit of how much you do) when you want a very particular layout for the city, and also gives me some flexibility.
Also, if I decide to redraw roads once the buildings go in, it's relatively easy as a process to tweak and edit. I can either redo the method, or just nudge the existing buildings to fit.
A small teaser, including some proof-of-concept city work, and the basic outline of roads and maps.
It's worth noting that this is nothing like my first draft other than the river and castle placement. I suffer from an addiction to second-guessing my decisions.