(I'm sorry for replying to the wrong message. I lost Jimbo's original posting in an internal mail misconfiguration.)
Jimmy Wales wrote:
I would like to gather from the community some examples of works you would like to see made free, works that we are not doing a good job of generating free replacements for, works that could in theory be purchased and freed.
There are lots of contents that could (and should) be free, but is still under copyright. Some are in the hands of museums and archives, some in publishers, some in government agencies.
I think it would be a mistake to start pouring money into such institutions, which should instead be forced (by a change of copyright law or national policy) or encouraged to give it away. We'd run out of money much too soon, and we'd build expectations that old collections can bring profits.
Take for example Anthere's recent report [1] from a conference where she told French policy makers that we can have NASA's public domain images for free, but can't afford to pay for copyrighted images from ESA (the European Space Agency). As Wikipedia gets more attention, this argument grows stronger: ESA should (be forced to) free its images, to match NASA's offer. Starting to pour money into ESA would be very contraproductive. More money would in fact make our dream a lot smaller.
[1] http://mail.wikipedia.org/pipermail/foundation-l/2006-October/010854.html
Something I believe that money could do is a system of travel scholarships for young Wikipedians (say, under age 25) who want to travel to a foreign country for a few weeks to gather facts (and photos) that will then be published as free contents. Even if we can't really require the results to be useful, the system is still not likely to be abused because it can only be used once or twice by the same person and the application process would include recommendations from the community. The amount necessary to cover the cost for affordable travel and accommodation is not very large per person (say US$ 1000 or 2000, for example a European Interrail pass for two zones and 22 days is UKP 200 = US$ 300), but it can mean a lot to the individual. A donation of $100 million would be enough for 1,000 such stipends per year for the next fifty years. Or rather, a $200,000 fraction of that donation would be enough for an initial trial of 100 to 200 such scholarships.