Well, there is certainly more to this project than I realized, which is good. I'll be learning a lot. It also means I won't always have amazing stuff to post, but I will keep updates going and try to explain what I'm doing as I go along.

Also I've decided to keep it at 100px per inch. I started building it at 200 but the file is already over 1GB and I've just barely started. I thought about working on the map in pieces, but there are a few elements that span most of the map (streets) that I'd have to make sure fit together, and a few of the operations I want to run will be easier for me to manage if I'm working on a file that is the whole map. I'd still like to figure out a way to produce smaller sections that fit together, but that may be next project.

This is the Illustrator layout file. I like using a vector program here because it is so easy to move things around and edit. Also my cobblestone streets are Illustrator brushes so that's where I start. In an older version of this I had a bunch of separate buildings; this time around I'm going for more of a medieval over-crowded city feel, where the houses and shops are all stuck to each other. We'll see how it goes.
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Then I start pasting things into Photoshop. I was thinking about really streamlining the map, for example having all the floor surfaces be on one layer, but I realized that the pattern overlays are not going to work well with that. I'll need to make each floor a separate layer and figure out a good way to align the patterns.

Next step is probably to try out some wall styles to see what I can come up with that looks half decent!
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@Invictys, I checked out the map, and thanks for the link. I hadn't originally planed on any rough stone surfaces in this district but now I'm pretty much sure I'll find a place to use those techniques.

@Jacktannery, I need some work on city maps too, so here's hoping I'll figure some things out as I go.

Thanks for reading!

cheers,
Meshon