The disastrous Trump months vindicate this - Trump has not hesitated to sign an epic arms deal with Saudi Arabia, throwing various rhetoric to the side with much less nuance than Obama did. The links between terrorism and the Sunni states has continued to fracture as well, as a large scale war threatens to break out with Qatar and Yemen as battlegrounds.
One thing Dave Chapelle said, just as he said that he would "give Trump a chance," is that we may end up missing Obama. The inferno that ended up leading toward Trump was there during much of those years - I wrote about it all the way back in 2010 or so. While it is disappointing that it was not stopped, it's questionable what could have been done to do so. Much of the chaos of Obama's second term ended up associated with him for some simply because it was there - its acceleration toward climax with his absence may indicate an eventual redemption of his legacy.
France's President Macron has declared that there is "no legitimate successor to Assad" and Trump is disliked and America declining enough that another Western adventure in the Middle East is something we no longer need to worry about. That part of history may soon be over. With it, the question mark of Obama's legacy may, in the long run, have a good answer.
Barack Obama most likely will be remembered somewhat like a mix of JFK and LBJ - a president who presided over dramatic social change which transcended his own term. Whoever succeeds Trump will be the one to finally fix things back in to shape and to create some order out of the destructive chaos we are in.