First, let me start off by saying that I'm a Canadian citizen, and have been for my entire life sauve the first 2 years. I have spent quite some time in the USA, everywhere from Florida, to Phoenix, to Maui to Pittsburgh. I love America, and I've often seriously thought about going after a green card.
Now, one thing that I COMPLETELY hate is the American health care system. A system where you have to pay for health care insurance, and even then, depending on your policy, you might still be SOL. Some will disagree with me, but in my opinion, health care is a universal human right. It should not have "user fees" attached to it. A person should not have make a choice between their cancer medication and their mortgage, or putting food on the table for their family. I love Canada's universal health care. Some will argue that yes, we pay more taxes (it depends actually, sometimes it's pretty dead-even with the US), but I wouldn't trade our universal health care for an extra $10K a year on my pay cheque, not a chance. Afterall, what good is money (or anything for that matter) if you're dead.
As for Obama, remember that he's got a lot to deal with. He was left with over half a trillion dollars of debt, a broken economy, a mortgage crisis, unemployment that skyrocketed, and of course 2 wars, one of which is a complete mess. The president could have been Obama, Biden, Palin, McCain, it doesn't really matter, because a huge political, financial and military mess was left from 8 years of W holding office, and that doesn't get cleaned up in 1.5 years. My opinion anyways, as an "outsider looking in".