I have Obama as pretty clearly the best president of my lifetime (Bush Sr. to present). I also consider him to have plenty of flaws worth discussing and critiquing as we move forward and try to improve policy. My two issues are:
1. The deification thing that some centrists do for the guy (not all of you, a small but vocal contingent that we might as well use Neera Tanden to symbolize). Knock it off, everyone has flaws worth critiquing so we can improve our strategies going forward.
2. It feels like people give him more flack than deserved on certain issues when a) the politics of the day were way more limiting in terms of what he could push through and b) the obstruction he faced was unprecedented so while it's easy to blame him for attempts at compromise, him being surprised at it is not an unforgivable miscalculation.
3. I truly believe that his legacy will be hard to measure thanks to Trump kamikaze'ing most of Obama's most forward thinking plays. The Iran deal and the overall foreign policy philosophy being the one that sticks out. I think we were just starting to get on a new track but it got derailed before fruition.
If we go back over basically everyone who has run this country, I'll always come out with more complaints than positives. But I think the BIG policies are the ones that we tend to think of and define presidents off of. For Obama that's the ACA and getting out of the recession. All circumstances considered, he did well with those even though I don't agree with every strategy/idea he applied. Now, revisiting Chomsky's quote though..."no relevant change" has a chance of being legit but that's impacted in large part because of who followed him and the Dem leadership's failure to defend his legacy more aggressively.