I have now updated my previous map sketch, and it looks a lot more like what I have in mind. The scale is tentative, as I am not trying to draw an entire continent, but I do need a fairly large area for the region where the game begins.
Again, this was drawn with a pencil on a sheet of basic printer paper. I embellished it with colored pencil this time, though. I added some shading, traced rivers in blue, and used red for the Trade Road. I also added some rough hatching where I think I want significant forests. Dots indicate both major population centers and potential sites for ruins and quests.
Everything is still subject to change, but this is definite progress in the right direction. Please coment below with questions or suggestions!