Things are progressing with the tiled half of the set. This is a 'Map file test', where I set up the new buildings in a circular array to check that the map files are working as expected. The buildings on the outside edge haven't been finished yet. I've tried to take on board all the useful and helpful advice from earlier in this thread - in particular the photographic evidence.

I've changed the dormers for you, Wyvern :)

These appear only on the larger houses in the set - the richer merchant style houses. I'm just testing them on the only tiled house I've made so far, which is the smallest one.

Remy's suggestion is a good one, but maybe (and this is only a maybe) you could tackle it the other way around - make the mountains first and then a soft edged pass between them, a bit like drawing a river in the lowest point?

Do you have City Cliffs - the 2020 Cartographer's Annual? Not a problem if you don't, but if you do you could use the cliffs as rocky bluffs a bit like this. (Sorry about the crude 5 minute drawing).

These are city scale cliffs, but if you use them more as rocky bluffs at dungeon scale (I assume it's a dungeon scale map you are making) you could build up level on level - maybe use different rocky textures instead of grass.

Another idea is to add a sheet similar to the one in SS5 with a hugely blurred Bevel, Lighted effect on it to draw transparent polygons on it for hill shading. I've got one here in the style I'm working on.

You could use a combination of both those things, or combinations of other techniques, but the main suggestion here is to start with the terrain and not get stuck on the path itself. That can be added at the end when the terrain is done, and might even be a result of the terrain, rather than having to be specifically drawn in as a path.

Having fun with different kinds of dormer. This is the same basic building...

Something a bit like this, then... Or is this too melted to go with the thatch?

Oh shoot! I forgot to cut the chimney extent out of the map file, so its a lot brighter than it should be, but you get the general idea.