A good point, I didn't actually consider it. Just started drawing squares to fill the map with buildings. The buildings should definitely not be so symmetrical, should be in varying degrees (as you said, no so 90 by 90) and should also be less rectangular. What I know from medieval building, particularly when it came to peasants, they were built from boughs, mud, and poo (not kidding). Not sure how I could do that in photoshop though, at least other than painting each building by hand.

Not opposed to painting them by hand but I only have a pc mouse to play with. Don't own a pen, which would make it a lot less painful. I literally hurt my hand painting/coloring those trees one by one