It's a disaster waiting to happen.
O'Reilly will be hostile from the get-go.
A good journalist will cross examine their politician highlighting weak points in their overall policy giving the politician a chance to respond to the criticism and it is for the audience to decide if this is a good enough response. Not O'Reilly. When it's his show, his poisonous views are all you hear, and his audience follow him like the rats follow the Pied Piper.
He will talk over Obama and use it as an opportunity to show his Republican credentials.
The best Obama can hope for is withstanding the barrage from O'Reilly. I know some people will say that is good enough, but I don't think so.
Obama will be thinking that he will respond to irrational questions with rational answers. This simply isn't possible - you can't be rational with an irrational person, which is what O'Reilly is.
The interview will be a mess, and what do you think the media will do when this mess airs? They won't be criticising O'Reilly for being a disgrace to his profession anyway. Just like the Pastor crap, Obama will inexplicably carry the can.
This is a huge own goal for the Obama camp.
They should've picked a more credible conservative show (if there is such a thing).