The easiest ways to do what you want to do are with mapping programs like Fractal Mapper (TM) 8, Dundjinni (TM) and Campaign Cartographer (TM) 3.
I think that the shortest learning curve (a week to be an expert) is with Fractal Mapper 8. It's the program we use for our products. Unlike most other programs, you can try it out free and also get the complete tutorial documentation free. It has the shortest learning curve of the most popular mapping programs, but it also can do almost anything that any other program can. The trial version of FM8 is different from the full license version in only two respects:
1) You can't save maps with the trial version.
2) Fewer mapping symbols are delivered with the trial version.
You can download the trial version here:
NBOS Online Exchange
You can download the beginning documentation and tutorial here:
NBOS Online Exchange
You can download the advanced raster mapping tutorial here:
http://www.nbos.com/vintyri/pdftu01.zip
and the free supporting files for the tutorial here:
http://www.nbos.com/vintyri/tu01sptpack01.zip
There's no time bomb in any of these products. You can use them for as long as you wish.