Could he have done more? Sure. But he spent a lot of political capital getting the ACA done. Then he followed traditional political decorum when the GOP pushed him around that in hindsight was a mistake. If all the rules both written and unwritten are going to be thrown out, the obviously it's best for the person who throws them out.
This. There’s a deep vacuum of leadership in the Democratic Party. Obama is a widely trusted figure on the progressive side and has nothing to lose by saying plainly what everyone can see. Only Gavin Newsom has demonstrated a willingness to do this. At the Federal level, though, the leadership is MIA. I mean Obama owes no one anything now; but I do wish he would just say what needs to be said.