O'Reilly will probably ask him some hard-hitting questions from a conservative standpoint...but I don't think O'Reilly will be obnoxious to him. Bill O'Reilly is smart enough to know that there is a difference between interviewing some anonymous liberal and interviewing the President of the United States.
Are you coming to bed?
I can't. This is important.
Someone is WRONG on the internet! -XKCD
I think the interview will be fine.
First, realize the situation. Its the superbowl, its not a time for hard hitting, deeply indepth, deeply meaningfuly political questions. Its not the proper venue, nor audiance.
Second, you should show respect for the office based on this situation. Since this isn't a deeply political situation, some respect should be shown the office by not trying to make it into some kind of "gotcha" spectacle (such as the NBC interview that deliberately took Sarah Palin out of context to do so during the campaign).
Third, based on the non political nature of the situation and the generalized respect that should be shown to the office, the best bet is to deal less with ideological policy and more with general questions regarding now.
What was his feelings of his first two years? What was his feelings of the mid terms? What is his thoughts going into these next two years? Is he thinking ahead to 2012 at all? Does he have a particular item that is most important to him in the next 2 years (ala health care in the first half)? Does he have a particular item he thinks he could fully get behind that the Republicans are pushing? Who does he think will win the game?
Only one question really fully lets him go into agenda/ideology talk, and that's balanced by the question regarding working with the other side. The rest of it is simply allowing people to get some insight into how he thinks, which frankly could go either way depending on what side you're viewing it from.
On the flip side, I think its also encumbant on OBAMA to be upstanding in this as well. Its the superbowl, its non-political, its a friendly interview. Don't take jabs at Bush, don't take jabs at the republican congress, don't get overly ideological, and make it more personalable then lecturing.
I think, based on his "entertainment" type of appearances before, that he can do this. I also think, given O'reily's previous history of interviewing Obama and his history with these type of things...and his attitude during the election night coverage which I thought was excellent save for the one time he openly admitted he was getting nasty...that he'll be up to the task as well.
"I am appalled that somebody who is the nominee...would take that kind of position"
"A court took away a presidency"
"...the brother of a man running for president was the governor of the state..."
It's horrifying because Trump is blunt instead of making overt implications.
I just finished Pinheads and Patriots and--IMO--O'reilly ended up rating Obama 50/50 pinhead/patriot.