You are asking me an excellent question that I haven't really thought much about.
Off the top of my head, there are a couple of things to consider. You first said that education is a provincial jurisdiction. That is true. However, official languages are not. They constitute a matter secondarily associated with the subjects listed in sections 91 and 92. Certain Supreme Court decisions dating back to the 1970s tell us that. The Jones ruling comes to mind.
The Supreme Court put forward the idea, without elaborating on it, that it would not be impossible for Parliament to legislate on official languages in an area of provincial jurisdiction, on the grounds of its overall authority to make laws for peace, order and good government, and that official languages issues are sufficiently related to national unity as to justify federal intervention. Therefore we would need a Parliament that would try to do this and see whether a province would actually challenge that action. Perhaps we would find that the Province would be happy to see money coming in, even in one of its own areas of jurisdiction.
Also, we should not forget about the possibility of negotiating. Everything can be negotiated. That would be an easier way to get there.
In short, I've always found interesting this Supreme Court idea that Parliament has the overall authority to legislate on official languages. In fact, another related issue that interests me is the role that Parliament could play in regard to the City of Ottawa. Municipalities constitute another matter very much under provincial purview, but the nation's capital is a distinct city. The City of Ottawa is different from other cities. Could Parliament then pass a law or take positive measures to promote official languages in the City of Ottawa, when municipalities fall under provincial jurisdiction?
I wrote a paper on the subject and I think that the answer is yes, based primarily on section 16 of the Constitution Act, 1867, which declares Ottawa to be the seat of government, and on section 16 of the Charter of Rights and Freedoms, which stipulates that English and French are the official languages of Canada. I can envision federal legislation, on the grounds of those provisions. The capital city belongs to everyone. It's not strictly an Ontario city, even if it is in Ontario. Ottawa belongs to all Canadians.
I think that could justify financial and legislative federal action to promote bilingualism in the City of Ottawa. In fact, that is something I would like to see in the next official languages act. My colleague Linda Cardinal and I submitted a brief on this issue to the Senate, and we are preparing to submit one to you as well.