I've been making maps for Wikitravel for about 6 months, and have been trying to work out a consistant graphics style for Wikitravel destination maps which should be easy for others to use if they wish to. I started with Paris in part at least because I was there when I first started the map-making project. You can see a full list of maps and some of the reasoning on my Map page.
User:Mark/WWW-Mediawiki-Client is a perl library which provides a client API for the Mediawiki software. It comes with a script called mvs which allows one to edit a Mediawiki site using a normal text editor and commit changes and get updates from the command line, very much like cvs.
I've visited a number of places (other than the places where I've actually lived), and may or may not have something interesting to contribute about them. If you've got a trip to one of these planned, bug me and I'll put some time into the article.