I'm not sure anything more than further polarization would result by sitting with either. Both sides will claim victory and continue the divide.
If he sat with a major conservative player, I think the # 3 (conservative talk) Glenn Beck would be the best choice. Limbaugh and Hannity are Republican and very partisan. Independent (conservative/libertarian-leaning) Beck seems to be willing to engage in true conversation. Granted, he doesn't agree with Obama's politics (as with Bush's), but he respects political leaders that truly believe what they say. He seems to have a more moderate following and is usually willing give people of opposing views room to make their point...as long as they come to exchange, not spin.
The problem Obama may have in the Beck arena is that he (Beck) is hard to predict.
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