All in all, Obama has done very little to breach the growing economic divide between poor and rich Americans. While the poor remain stagnant and miserable, the rich continue to grow richer by the day. The problem is systemic and unlikely to be solved by any sitting present. Most probably, the divide will never be erased.
I think the old saying of "do not stab someone in the back 9 inches, pull out three inches, then celebrate your progress" is very applicable to this situation. Has President Obama worked towards leveling the playing field? Sure. Has President Obama leveled the economic playing field? Not by any stretch of the imagination.
I wish Obama would move forward on his plans to create jobs that would simultaneously rebuild the infrastructure in our own country. People need and want jobs. I am a senior and I need a job in order to survive on Social Security, but more than that I would like to feel like I am contributing to society. In every family, each person who goes from joblessness to having a job increases that family's economic playing field. Changing tax rates and fidgeting with spending does not do that much to make a society feel energized or believe that they have much opportunity to change their future. I see a sense of despair in my community.
To give a full answer to this question, first you would have to define what leveling the playing field means. Obama has done nothing to create new opportunities. Certainly as many disparities in net worth exist as always have. I don't see pro athletes and celebrities taking any pay cuts. Handing out a few extra dollars in tax money to some who may be more needy certainly hasn't made the situation any more level.