Q: What kind of software do you use to draw your maps?
A: First I find a base map in jpg or gif that shows the area I want to map - let's say China. I go to the CIA website and download their public domain map of China. Obviously, this map will have a lot of details I don't want, while lacking details I do want. It will have all the wrong colors, and it will be the wrong size.
No problem. All I have to do is manually trace a blank outline map, and fill in the details after that.
It's darn near impossible to trace a map using a standard pixel-based draxing program, so I use a vector-based drawing program instead. Specifically, I use a version of Aldus Freehand that's so old it won't even run on my current computer, which means that I have to keep an older computer set up across the room and then use a 3.5 disk to transfer the finished product to my new computer. It's so old that Aldus stopped making Freehand years ago.
Then, I copy and paste the finished product into Paint Shop Pro, a pixel-type drawing program. This transfer is when I adjust the size the map will have on the screen. The transfer also tends to distort any lettering, so I've learned to not put the labels on yet. It also distorts any color that isn't one of your pure primary colors, so again, I've learned to hold off on the colors until after this step is complete.
Here's where I label and color.
To make the moving maps, I use Alchemy Mindworks GIF Constuction Set.
There's probably an easier way to do it, but if it works, it works.
I can't endorse any specific map-drawing software since I don't use any, but Centennia seems to be fairly popular, and I've played with their free Napoleonic maps, which are pretty cool.