Reverting back to the headline and Obama's management of the Levantine conundrum, I'd say he has actually handled it poorly. Since 2011, the R2Per's, neo-Cons fixated on maintaining Israeli strategic preeminence in the ME and an assorted bunch of regional powers pursuing their regional objectives ( to which they are entitled because they live there ) have pulled him hither and tither. HC as Sec of State used the opportunity to ingratiate herself with potential future donors with deep pockets. Her upper management at State was staffed by ideologues like Nuland, a professorial class whom saw realism as effete. So, Assad had to go. To this day, no one has come up with why that is a US problem save a self-serving "abdication of global leadership" position (recall the Israeli minister's wife's description of Obama).
As illustration, re-release Obama's Cairo speech. It reads like an affable IR grad student's wish list.
The Syria policy is a mess and we're dealing with cunning "allies" like the Tayypists and the Qataris. Netanyahu needs to goad the US to further Israeli agenda but Obama sees that now and has retaliated with the Iran deal. Turkey knows intimately IS's leadership and hopes to control them with the promise of a self governing space in the future.
Overall, there are just too many moving parts for any US president to bog themselves down with over an 8 yr period, but BO has managed to lose everyone's trust by being ideological and not a realistic.