I think it all really depends on scale. In my Northmark map, looking at it again, I feel like the scale is off. Looking at the size of the buildings and the width of the towns (the majority of which are supposed to be quite small), I think I goofed. I should've made the scale 1 inch = 1/2 mile or something, or greatly reduced the number of buildings in each community.

So for your country maps, my thought was that the scale is still too large to show even a generalized shape layout of the cities, etc. unless either A) the countries are tiny, or B) the cities are freakin' HUGE.