1) Do not make fun of Donald Trump
2) Encourage Hillary to remain a Senator
3) Go all out on healthcare; work with Sanders and Feingold to get Medicare for all passed
4) Push for the reinstatement of Glass-Steagall
5) Avoid the TPP
Why 4)? Dodd-Frank is more far-reaching than Glass-Steagall ever was. And the main failures were pure investment banks or pure commercial banks, both of which wouldn't have been affected by Glass-Steagall. Goldman Sachs and Lehman Brothers (before it collapsed) couldn't care less about Glass-Steagall. And even if banks with both investment banking services and commercial banking services failed the problem isn't the fact that they combine both services, the problem is that they screwed up both services. It would be more logical to just regulate investment banking and commercial banking more if you want more financial regulation. Heck, commercial banks and investment banks were merged during the financial crisis to strengthen stability (wouldn't have been possible under Glass-Steagall) The amount of glorification Glass-Steagall gets is ridiculous. I understand why liberals want more financial regulation (though I'm not really sure about it myself) but Glass-Steagall wouldn't solve much.
Anyway, I'm not sure whether Obama would do a lot of things differently (butterfly effect like someone said). He definitely would have forced everyone to use their work email and he would have tried to stop Hillary from giving Wall Street speeches. He might have encouraged Biden to run.