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''Please import all appropriate images from a whole category at one time and then register the category on Wikimedia Commons that they were imported from here.'' I mean let's systematically work through the relevant categories on the Commons -- just write down which one(s) you've already been through so we don't repeat it, and do one at a time so we don't miss stuff. While you're at it, why not take a moment to help the Commons fix up some of their categories? Categories on the Commons do not have to be directly mirrored here. Please see the list of categories above, and register your new category there too.
''Is there a smarter way to do this? e.g. bulk uploads?''::This was the answer on the MediaWiki-L list: "For mass uploading, you might want to have a look at the Python wikipedia robot framework that implement an uploading tool: http://pywikipediabot.sourceforge.net/" -- I'm not sure that's the ideal solution. If we want to get all the information and arrange things in appropriate categories, we might as well do it all manually, even though that takes time.''