Frustrations with Art

I don't know what artistic directions to go. I guess I should have thought about it more. I was making icons but I dont know if I should make it: Overhead view, isometric view, or some abstract symbol. I guess I haven't done art enough to go by and make carefull thought of my assumptions. 

All i can do is the walls at a random angle. 

Some Walled City Icon for a hex map.

A walled town for a hexmap. 

I event went so far as maybe using Blender to make a simple town with simple blocks then trace it. Of course I need to remember how to use Blender after about 3 years of last modeling with it. :(

Anyway, work, the weather and my 18mo. old baby boy has been a useful distraction given how frustrating is the problem.