A small group of related questions for you guys. After following RobA's great tutorial I know feel comfortable (ish) creating general landscapes in GIMP, enough that I can experiment a bit and generally improve my work anyway.

However the problem comes whenever I try to place any towns or buildings on the landscape - they tend to end up looking like a 5 years old scrawl, hence I was hoping for guidance.

First Question is: am I a fol for trying this is a raster package rather than a vector one and importing?

Question 2a: If I am a fool what (preferably free) package should I be looking at, and is there another guide to get me past those first steps similar to the GIMP guide.

Question 2b: If I am not a fool, then can somebody sugegst where a look (another great tutorial would be cool) to expand my skills to be able to do this.

As a guide one thing I see alot of mention of is brushes, to me these are the circular (and occasionally square) things that you vary in colour and width and thats it, but I sense I am missing out on a whole arsenal of tools with this view