Automating the map creation process

There are several tools available that allow you to quicken up the map creation process.

Vision creation

You could just start with a map in SVG format. These can be most easily found on Wikimedia Commons or a Wikipedia in your language.

Various raster (ie., not SVG) maps are viable for conversion to SVG format - two most used tools for this are potrace (bundled with Inkscape, available as Path -> Trace Bitmap.. command) and AutoTrace (available for online use here). The clearer the map, the better results you can get - single-color borders on single-color background, or differently colored territories, work best.

Centerpoints

A tool that can create centerpoints is available on forums: http://warlight.net/Forum/Thread.aspx?ThreadID=2452. It calculates the centroid of every territory-polygon and places the centerpoints. It does not work correctly on multipart territories. Source code in Ruby available here: https://github.com/MatmaRex/Warlight-Tools

Connections

A tool that can create connections is available on forums: http://warlight.net/Forum/Thread.aspx?ThreadID=2668. It checks every pair of territories and every pair of their points - and considers them neighbors if the distance between any pair of points is less than 5 pixels. It does not work correctly on multipart territories, and can take a long time to finish (up to a few hours on large maps). Source code in Ruby available here: https://github.com/MatmaRex/Warlight-Tools