Some time ago I wrote a tool to facilitate the spread of images on wikipedia (which is mostly a good thing). However, it was very slow and not very user-friendly.
Finally, I got around to rewrite it from scratch (something we're all good at;-) and now call it V2.0:
http://tools.wikimedia.de/~magnus/missing_images.php
Basically, it scans through a set of random articles, or articles from a category, and checks if they have images. If they don't, it tries to locate images in the matching wikipedia articles in other languages. It also checks on their license status, and wether they're already on commons. If not, copying them to commons is assisted by my commonshelper tool.
If you find the tool mistakes some icon from a navigational element for an image, please add the icon name to http://meta.wikimedia.org/wiki/Missing_images_tool/Ignored_images
Also, feature suggestions and bug reports are always welcome.
Thanks, Magnus