I think what sticks out most to me is that your houses seem to be bigger than the hills. It seems like they should be mountains on a regional map. Also you have this artificial black stroke around them to make them look higher but it's too general in its use...broad shapes instead of minute detail. Lighten them up some and add more of them in the valleys and such cuz right now it looks like bumps sitting on top of plateaus. If it were me I'd scrap the hills/mountains altogether and just use a big light airbrush for some terrain sculpting (by hand as opposed to 3d rendering). And yes, the forests look too perfectly shaped...break em up some so they aren't so round and smooth. All in all though it's pretty decent and just takes a bit of practice to develop one's own style. Keep up the good work.
If the radiance of a thousand suns was to burst at once into the sky, that would be like the splendor of the Mighty One...I am become Death, the Shatterer of worlds.
-J. Robert Oppenheimer (father of the atom bomb) alluding to The Bhagavad Gita (Chapter 11, Verse 32)
My Maps ~ My Brushes ~ My Tutorials ~ My Challenge Maps
The edges of the forest, here is a quick and dirty edit on a small bit of your map using a layer mask and a big, fuzzy, low opacity brush with a few different colours on the background.