Wow, thanks so much for all the kind words. I linked to the map a year when I released the first version of the setting PDF - but had little response, so I'm a little overwhelmed from all this praise.
The map is essentially 6 years work, on and off (mostly off). Started out on a napkin, with the goal of making a campaign setting where "the far away lands" were real and, indeed Greylock, where there was room for both land and nautical adventures. My settings before this were always quite small, and I felt ready to tackle a large one now and go a little mad with detailing.
I've gone through 5 versions of Paint Shop Pro while making the map. Version 5, 6, 7, 8 and 9. The middle continent, Centar, is mostly done in version 5, and if you look closely you'll notice the text looking a little different, more smudged, on this continent, since version 5's text rendering engine was different back then.
The visual style and palette of the map is inspired from a campaign setting called Erathon, which I saw many, many years ago. I decided to use his/her's colour palette and everything sort of grew from there (the last link I can find for this setting is
http://www.iei.net/~mkletch/ but the setting has been taken down, it seems). If the maker of this map lives on this forum, then perhaps I could get his permission to upload his map for comparison.
There's no real technique used, except lots and lots of layers in Paint Shop Pro and lots of pixel pushing. Even today, with 1 GB of RAM, I can't hold the full map in memory at once, but have to edit continents separately and then merge the layers and assemble them in a final version.
I start with the black coastline border, then select the innards of lands so make sure I don't stray outside the coastline when painting terrain. In order, the layers are listed below. Unless noted, they are all bitmap layers.
Background
land
waste
terrain
borders
mountains
rivers & lakes
black border
roads
icons
colour under names
names
location names (vector text layer to bend and shape text)
After the land has been painted I place down chunks of mountain. As I get closer the the edge of a mountain range, the chunks get smaller until I place individual mountains. To achieve the layering effect, I have to start from the top, so the mountains are always a bitch to place and I breathed more easily when that was finally done some years back.
Afterwards I draw the forest, in a solid green colour, lock the transparency of the layer and then paste patches of forest colour variation on top. Locking the transparency ensures that only where I have painted the green forest colour will the bitmap be pasted.
Finally icons and roads. As a general rule I try to make cities and roads follow the terrain, and not the other way other, but occasionally I do go back to remake parts in case I'm looking for a more dramatic geography.
Eosin, there are little thorpes at road junctions, you just don't see them (if that isn't the most hand waving answer, I don't know what is

). The smallest village I decided to draw on the map is 900+ residents. When everything is done, I might go back and add more detail, perhaps thorpes and hamlets under 900. About the river/mountain crossover: Yes, you're right. I'll go back and have another look at it. The borders, I find, are easier to spot on the uncompressed map, but they are almost impossible to see here. Especially since I think the land and border color is one of the color combos colorblind people cannot see properly.
Bjorn