Obama has gotten more done then any President since LBJ......so I would say no his personality isn't crippling his presidency.
Yeah, lots of watered down pieces of legislation. The impression I am getting in Double Down is that Obama hates the Presidency, and hates elections, but continues onward due to ego. His White House staff was in chaos in 2011, with power struggles against Valerie Jarrett in particular causing a lot of tension.
You should finish the book. A passage I just read during Obama's debate prep that seems to pertain to this thread: "Axelrod and Plouffe thought something more radical was in order. For the past six years, they had watched Obama struggle with his disdain for the theatricality of politics-not just the debates, but even the soaring speeches for which he was renowned. Obama's distrust of emotional string-pulling and resistance to the practical necessities of the sound-bite culture: these were elements of his personality that they had accepted, respected, and admired."