I've been experimenting recently with recreating various map styles with my procedural techniques. The first style I've attempted is from a 1914 Hammond atlas:
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It was a cheap atlas, and it shows; registration is pretty iffy, there are ink blobs and stripped characters (there's supposed to be a dot in the middle of the "capital" star for Kingston, for example), and the label placement is pretty sloppy. Still, it's a fairly simple map, so a good first attempt.
First off, I grabbed geodata of Jamaica's coastline, cities, roads, and rivers; these are from different datasets, so they don't quite mesh up, but the effect is there:
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The first thing I do is place the city circles; coastal cities are placed so the circles osculate the coastline (except for the capital). This is easy to do procedurally; just find the closest point on the coastline and move the circle towards or away from it:
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