I think this is a really nice map though I've never attempted one in this style so I can't really add much. But maps like this always tempt me to give it a try.

The shadows thing is a huge pain. On my own maps I've basically had to add big shadows by hand because of how drop shadow works. I keep meaning to take a look into whether there is a photoshop filter plugin in that simulates proper cast shadows but I always forget.

Also, that regional map looks great.