I'm not just trying to play defense here, but how much of that stuff represents Obama's policy preferences, and how much represents what he could accomplish given the lay of the land in Congress, especially after 2010? The prioritization of health care was largely his choice, but it's not clear to me that Congress had an appetite for more stimulus or more financial reform than they passed, even if it wasn't enough. I'm not sure how/if Obama could have done more (with the exception, of course, of holding the heads of the institutions that caused the crisis accountable, to prevent the moral hazard in the first place).
Everything outlined here was a matter of choice, not necessity. Look at who Obama appointed, his executive choices, his major addresses, and his general rhetoric.
Of course there's no guarantee that legislative outcomes would have improved. That's impossible to demonstrate (and therefore always the first choice of objection for his defenders). But decisions like appointing Tim Geithner and Larry Summers, starting a drone war in the Arabian peninsula, or devoting much of his second term to promoting an unpopular international trade agreement were all just that: His decisions.
pushing for the TPP was the right thing and still is the right thing. Containing China and its illiberal and bullying tendencies is important for the future of the free world.