I am a newcomer to Wikimedia/Wikipedia and do no know enough about the organization and its structure internationally. My comments are offered in this light.
Any organization which wishes to remain viable for an extended period of time needs a dependable source of funds that are not dependent on the vissitudes of fundraising from individuals and/or foundations. Although some more established NGOs have been raising chartible funds long enough to have developed a following with a base large enough to assure certain minimum annual income, these organizations, because they usually provide service, have developed a flexible model that allows them to alter the extent of services based on actual income.
Wikipedia seems to need to continue to build and service a population that does not allow for swings in fund requirements. It has been able to build its network over the past several years by mostly special grants that might not be there as a permanent source. I don't know what minimum cash flow is required to maintain its network, but Wikipedia probably does not have the flexibility to curtail its international support. If or when Wikipedia has worn out its realtively limited financial supporters how would a collaspe of the network be avoided.
Wikipedia has intrinsic value as evidenced by the many efforts to convice the founder to convert it to a profitable business. I understand how solid the stance against any changes in Wikipedia's model to offer free information. The threshold question is what does Wikipedia have that is valuable to those who can not or do not use it for its formative purpose.
I was at a lecture last night at the World Affairs Council about climate change. The speakers were distinguished authorities in the field of measuring the impact and working on plans, at the highest level, to try to deal with this phenomenon. It was clear to the audience that the public is not aware of the facts that we all face and how desperate the risk. Their words and charts evidencing their research does not reach a very large audience through their students and lectures. What role could Wikipedia play, in an organized fashion, in being part of the dissemination of this knowledge? Perhaps it is already there in Wikipedia but not in the form of a campaign that allows people with limited knowledge of the research techniques necessary to learn and thereby join the support for action. Getting the word out is part of the task of the climate change community and one for which they now pay a portion of their grant funds to accomplish. A cause worth doing and revenue as well.
One could substitute many particular communities that need to reach a large international audience and expect to help pay the cost of that contact.
I have other thoughts about the questions but will do that later.