A $3,000 bribe is not going to get you far. Studies have shown that Canadians would benefit handsomely, economically, from annexation, in terms of lower consumer prices, lower taxes, lower debt service on the national debt, which was, at least until recently (I haven't seen any figures since Dumbya doubled the national debt here), higher per capita than the U.S. national debt.
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There are far more valid appeals to Canadians, Australians, etc. With each area, different things might appeal. For instance, Australia would assuredly see an increase in white population, which does matter to them. They would also be assured that the U.S. would not abandon them to the 'tender mercies' of the Butchers of Beijing. This is one reason I am so ANGRY at FDR, because he could have told Australia in WWII that "yes, we'd like to help you, but we are NOT going to put our people in danger for you unless you join our Union. Then we will fite to the death to protect you. If you are not willing to join our Union, then make your own best deal with Japan — and start learning Japanese — because we won't lift a finger to defend you."
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Canadians like to think of themselves as enlightened, a force for good in the world. But of course Canada is not a "force" for anything, because Canada is NOTHING in the real world. As part of the United States, however, Canada would have a HUGE impact on the world, by altering the stances of the U.S. Government, helping to pass universal healthcare (which would allow Canadian retirees to move to the Sunbelt year-round without having to spend some time in the Great White North just to keep their healthcare coverage), reverse antigay legislation, and put reactionaries permanently in the minority, a helpless minority that can't even threaten a filibuster because they couldn't even remotely get the votes to stave off cloture. And the idea that key posts in an American Administration could go to Canadians, and that anyone born a citizen of Canada could run for President of the United States -- that's the kind of thing that can appeal to Canadians' sense of their own 'rightful' place in the grand scheme of things, a scheme they can now only watch from the sidelines.
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Puerto Rico statehood always has a constituency: the Latino population that is now and will for a long time be underrepresented because most Latin American immigrants, legal or illegal, cannot vote. And the idea of a Latino President of the United States from Puerto Rico appeals to the 'orgullo' (pride) of all Latinos, who are now the Nation's largest minority. Once you get people talking about Puerto Rico statehood, you naturally have to talk about the Virgin Islands, which is predominantly black. So a black President should be favorably disposed to making more black people first-class citizens. Obama is from Hawaii, and there are a lot of Americans who do not understand why we have colonies in the Pacific, since they could obviously all be merged into Hawaii. So we could tidy up the map and end the embarrassment of colonialism on Obama's watch. Once you break the powerful round number 50 (states), and have the untidy 51, the mind will be open to rising to the next round number, either 55 or 60. Mindset matters, and once you break the 50 barrier, other things suddenly become possible, especially since you simultaneously show that the Nation is still growing!
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To say that a President of the United States would not want Canada is like suggesting that he wouldn't want trillions of dollars of resources and tens of millions more prosperous citizens with which to meet the Nation's international responsibilities. If somebody walked up to you and said, "How about a million dollars, buddy? Would you like it if I gave you a million dollars?", and he lays out perfectly reasonable conditions, such as you use it for education and healthcare (for yourself and your family) and paying off debt and donating to your favorite charities, and educational foreign vacations, but not for anything frivolous or bad for you, like drugs — would you say "No way, man! Get out of my face!"? Would you think that a million dollars would create more problems than it solves? I wouldn't.
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As for how a President would broach the subject to Canada, the Philippines, etc., there are many ways. He could just say it, aloud, which would get the whole world abuzz. Say, he receives a state visit from the Prime Minister of Canada and at the foto opp or joint press conference Obama simply says something, even casual, like, "The United States and Canada are good friends and good neighbors. But I'm not the first American to think that we could be much more. Benjamin Franklin, Walt Whitman, the framers of the Articles of Confederation, and many other Americans have always thought that Canada and the United States belong together. Think about that, people. That's all I'm going to say about that today. But think about it, on both sides of the border." What would Harper say? How adamant could he be in saying thanks but no thanks? Would he dare to claim that no Canadian wants that? If so, Obama could say, "On the contrary, I have seen polls that show Canadians have thought about it, and, if the terms were right, a great many would welcome the reunification of what used to be a united North America during the British era, save that Britain wouldn't control, but we, together, would. Heck, I'd even welcome Britain into the Union for that matter, as a partner and integral part of the Union, of course, not as colonial overlord. We have so much to offer each other. If Europeans who used to kill each other every 20 years or so in centuries of warfare can join in a European Union, why can't we go farther?" Etc.
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Or how about this? He could avoid the possibility of being opposed by Harper or such at the same time as he mentions the issue by approaching it in a separate setting, such as a press conference. He could approach the whole idea of a larger Nation by addressing the status of Puerto Rico. He could make an announcement at a press conference:

Ladies and gentlemen, today I'd like to speak to the issue of second-class citizenship and American colonialism. I am embarrassed even to have to admit that the United States has colonies, and that there are millions of U.S. citizens who cannot vote for President and Congress. If there's one country that should never have had colonies, ever, it is the United States, which denounced colonialism, went to war over it, and freed 13 colonies in so doing. But we do have colonies, and I want that national disgrace to end. Puerto Rico has been dithering about status for decades, unable to make up its mind. Puerto Rico has been a colony of the United States since our victory in the Spanish-American War in 1898. That is much too long. Even if we could make excuses for why Puerto Rico wasn't ready for statehood or independence in the first few decades following accession, no such excuse has held water for at least 50 years. It's time to move the question. If Puerto Ricans can't make up their minds, Congress can. I can. Puerto Ricans can accept what we offer, statehood, or go their own way. And godspeed to them if they choose independence. But we have budgetary problems and need to spend American taxpayer dollars first and foremost on Americans. So if Puerto Rico becomes independent, it will be on its dime, not ours.

We have a second colony in the Caribbean, right nextdoor to Puerto Rico, the U.S. Virgin Islands. That colony's people, almost all of them black, cannot vote for President and Congress either. That offends me. The U.S. Virgin Islands is too small to become a state to itself, so I am asking Congress, which has the absolute power to dispose of the territory of the United States, to merge the Virgin Islands into Puerto Rico; create the two present territories into one state; and, in the plebiscite needed to rafiy statehood, count the votes in both territories as a unit for purposes of accepting statehood or voting for independence, the only two options. Voting for statehood will produce statehood. Rejecting statehood will produce independence, for both territories, and the United States will have no further financial obligations toward either territory, tho individual citizens will retain such rights as they individually are entitled to, including the right to move to the United States mainland. Anyone who accepts the citizenship of an independent Puerto Rico/U.S. Virgin Islands will by that act forfeit U.S. citizenship and lose all rights to move to the mainland. It's time for the people of our territories — all our territories — to step up to first-class citizenship, with all its responsibilities as well as rights. And while we are redrawing the map, let us throw our minds open to wider annexations, to bring into our great Union other areas with which we have so much in common, and get some help in meeting our worldwide responsibilities.

The United States is a great country, but only a small portion of this planet. The problems of this planet threaten to destroy us all if we cannot get on top of them and solve them thru joint effort. We cannot do enuf at our present geographic and demographic size. So either we accept failure, and its terrible consequences, or we accept that we must grow to prevail, and take judicious steps now to secure the future of this Nation, and this planet. Today, we start the first step, erasing the stain of colonialism from our national flag. Maybe we'll add a star. Maybe we'll cut our losses and see our national territory actually shrink a tiny bit. But our conscience will be clear, and we will be ready to offer equality within our Union not just to Puerto Ricans and Virgin Islanders but to other people in other places important to us. I won't list those places right now. Everyone within the sound of my voice may have their own list. Good. Think about it, pro and con. Think about it, talk about it, and let us see what we can agree on.

- posted by L. Craig Schoonmaker @ 2:48 PM