Regarding fundraising. From the recent discussion I've come to the conclusion that there isn't a fundraising committee, yet, so when there is one, I'll forward such ideas to it. But in the meantime, here you go.
I think there is a lot of untapped potential in selling existing WM items to try and increase the average donation. 'sweeteners'. The CafePress merch at the moment is a little bit crud. For example some Wikibooks already offer PDF versions (well, Learning German in English does, at least). So you could say, "Donate $X and receive a free e-book to learn German!" Or a "best of" the cookbook. The only extra cost to the Foundation is the bandwidth.
I am constantly amazed at the quality of Wikimedian photography at the Commons and we could easily bundle, say, 10 super high quality images together in a ZIP and offer "10 free computer wallpapers". Since we have so many I think we could even offer a choice between a few of these, by theme (eg landscapes, art, sunsets, science-y, insects having sex). We could set the donation bar for this $5 higher than whatever the average donation last time was.
I would also like to create some templates and put together some themes to allow people to easily make their own calendars from Commons material. And back to fundraising, CafePress does calendars. I don't really know who controls all that but I assume there'd be no objection if I/we put some together for that? I imagine they would sell really well in Nov/Dec. They also do prints and mousepads, gift cards...
Of course the markup on CafePress stuff is not great, it would be better if could be done inhouse somehow, but I haven't figured out a good solution to that yet. The "computer wallpapers" and PDF books stuff exists already though. I guess all you would need is to have the files on the foundation wiki and when a donation is over the target, they get some special 'download link'.
So, is what I'm proposing technically feasible, is it a good idea or will it probably be a lot of fuss for negligible impact, and should I start trying to find good candidates for such things?
cheers, Brianna en|commons:user:pfctdayelise
PS. I also think there is great potential in the Spoken Wikipedia material, but I haven't figured out what the best format for it would even be. How many could you reasonably ZIP?