Greetings cartographers

This is my first post here because I need some general advice.
I have always liked creating maps in fantasy setting but ... manually.
Today I decided to try the next step which is using a software.
So I took on of my maps, transformed it in .bmp.
Then I selected Wilbur because it is this kind of maps I had in mind.
Read the .bmp in Wilbur and wanted to experiment.
My problem is three fold :

1) I couldn't find a tutorial for Wilbur. The number of commands and options is astronomical so that finding out how it works by experimenting is out of question. Does a tutorial exist ?
2) My target is to take the outlines of the continents&isles I created and put textures/elevations on it. Is Wilbur the right software ?
3) Is it posssible to define just a contour map and to fill it inside (mountains, lakes, forests, cities, deserts) so that the coasts become fractal, the mountains appear with different heights etc and choose the colors ?

I apologize for what may seem super newbie questions but that is what I am.