One of the greatest shortcomings I see with Wikipedia and Wikimedia projects is with our use of maps and geospatial data.  I have seen ideas here and there on this mailing list and other places, but it's a big issue to work through.

I have background in geography/GIS, ability to use state-of-the-art software such as ArcGIS (http://www.esri.com) that is generally beyond the means of consumers, and knowledge/skills on how to use it to make maps for Wikipedia.  But, the potential demand for maps on Wikipedia is very high, the process of making them can be time consuming, and the number of Wikipedians to fulfill it is limited.  I did one a while back for Shoshone National Forest.  I could refine the look of this map, come up with some standard, and given lots of time could make one for every protected area in the U.S. (and then there's Canada and other countries). Despite this possibility (with significant effort), I'm not entirely sure having only static, non-interactive maps (quickly can become outdate) is the way to go.  I could probably write scripts on the GIS-end of things to help automate it, and a bot on the wiki-end to ease the process. I have also played around with the MediaWiki source code and been learning about writing extensions.

Also it would be fantastic to be able to use resources such as the "collection of rare maps of Africa, dating from 1530 to 1915" that's been mentioned.  Depending on the map, sometimes it is helpful to georeference them (geoTIFF is the format for this).  Also, check out http://www.lib.utexas.edu/maps/faq.html#3.html (see "Where are the rest of your maps?")  And, the map library at Penn State ( http://www.libraries.psu.edu/maps/) is quite extensive. 

I know it's a significant undertaking to develop/integrate any capability beyond static maps.  It's beyond the scope of what Brion and the current developers can handle, given our current resources.  But, I think we could use some discussion to learn what kind of maps/mapping/geospatial data capability that people would like to see with Wikipedia?  If given more resources, such as support from a grant, along with well developed and thought out ideas, and interest from the community, I think there is possiblity to improve from the status quo. 

I have put some more detailed thoughts about this issue here - http://en.wikipedia.org/wiki/User:AudeVivere/GIS   
I mention issues concerning locator maps for articles, offline maps/resources, GIS data resources available, copyright issues with data from some sources, open source mapping/GIS capabilities that exist, previous/current efforts - such as geocoordinates in articles, and other ideas. Feedback welcome!

If this interests people, I think we could work to develop specific, feasible ideas.  I also have knowledge about writing grant applications and would be glad to help.