For the record, I think Barack Obama has been a pretty good president. Like all of them, his record is a mixed one to everyone but those who come to it eager to say "He did everything right" or "He did everything wrong." I have a few friends in each of those categories and I've learned not to discuss the matter with them because they're not interested in the actual record; just in some validation of a view they formed long ago.
New York magazine has some really good pieces for those who are interested in a real evaluation of the man's eight years. There's this timeline of the events of those eight years, some of which involve President Obama and some of which don't.
Then Jonathan Chait interviews Obama about the challenges he's faced, most of which were from Republican obstinance. I am still not happy with everything that involves drones and the killing of people overseas but it doesn't shake my endorsement of the view that for much of his term, Obama's been the only grown-up in Washington politics. I believe history will view this man very well.
Lastly, I would also recommend this conversation with Vice-President Biden. There are a few places where he sounds a bit like Hank Kingsley talking about Larry Sanders but I think Biden looks pretty good as he gets close to stepping-down. And they also have an interview with Bernie Sanders about Obama's record dealing with Wall Street. All of this is well worth reading.