I read through most of the thread (whew!), and I must say I really liked the first version of the map. The second one is good too, but as others have noted, try not to mix styles (the hand-drawn mountains and the height map shadow). They can both be very nice on their own but not together, in my opinion. Also, I would suggest complementing the hand-drawn mountains with some minor hills here and there in the rest of the map, to suggest a more varied terrain. Plus I would get rid of the coloured borders, they are mostly distracting in this case, especially in the independent regions.