Robin, I moved this thread to the Regional/World Map Forum of the WIPs (Work In Progress). The WIPs are used to help develop a map that you are working on and the General Discussion forum is more geared to more of an off topic discussions or those that are of a more overall mapping interest. I know there are a LOT of different forums with all kinds of info in them so it is quite confusing to new members but I am sure that you will get the hang of it

Scale is another thing that would effect how many settlements are shown on a map. If it is a large area covered I would doubt that all the whistle stop villages would be on the map, unless there was something that was special about them (junctions, fords, bridges ect.) Just like not every stream or road will be on the map, not all villages will. The cities and larger towns most definitely would. Also consider that the larger the city, the more satellite towns and villages it would have in order to supply enough food for its inhabitants.

On the map itself, I think the trees, while I like them quite a bit, might be a bit big when compared with the mountains. Otherwise I like the style that I can see starting to develop as the features do have do work together and don't dominate any of the others.