The Ming conquest of the Tai-Yunnan frontier that I am working through with the Online Ming Shi-lu is geographically complex. I'm using three different Yunnan maps to figure it out.
I'm think of drawing maps, but why not just put points (for events) and lines (for military expeditions) in Google Earth?
Google Earth is being used as an aid for describing the geography behind historical events. There are some good ideas in the article linked to above. "Benchmarks: Maps of the World" in the "Journal of the Association for History and Computing".
"It is not hard to envision a computer lab full of history students who are geotagging maps of historic sites, using the information they find in primary source documents to create pop-up tags for particular locations.
"A good history classroom with beam projector and computer would be an obvious place for students to demonstrate these maps for each other, working with mapping, speaking, and document decoding skills.
"In a melding of technology and history a whole class could explore spatial data in making historic arguments."
Restoration of historical structures in a digital musueum is a possibility, the historian must "identify and geocode the structures that have been lost...find pictures that could be attached to maps—pictures and descriptive data that will preserve digitally what has been lost physically.
"One curator said that his museum will be rebuilt. Geocoded data could help this rebuilding process that will take architects, foundations, museum curators, and historians to accomplish.
"Using maps and information attached to maps, there are great possibilities for telling stories — histories — that might be lost otherwise."
Tutorials show how to add lines to describe paths taken and polygons to delineate regions. Download the "KML Tutorial File" which you can run on Google Earth to see examples.Superimposing historical overlays on Google Earth is also a technique.
There's a whole forum at Google Earth where people post their KML files describing historical geography with Google Earth.
You'd get a gazetteer if you hook a pedia (Wikipedia) to Google Earth with KML, then historical geography will be one click away with a suitable key word search at Google, searchable historical gazetteers.
Here's a directory of waypoints in Burma. Still looking for an extensive list of latitude and longitude points (aka "waypoints") I can run through a Perl script to create KML marking historically important locations and routes in early modern Burma in Google Earth. I found some snippets of KML creating code.
Here's a global gazeteer.