I agree completely with Pyrandon. Gimp is to my mind the most software you can get for your buck anywhere (which is of course no bucks at all). If you struggling to break into GIMP a good way to build up you confidence and skills might be to generate one of the cities in the RPG city generator that you mentioned and then just mess around with it for a while using Gimp. For a bit of a laugh that may prove quite useful run every script-fu on it and then take it from there.

I used the same generator and then toyed with it in gimp in my "Small Town" thread in the WIP section. Then just post something and the magicians on this site will come up with some incredible advice. That I promise.

Oh yes, welcome, welcome, welcome.

Torq