The trouble (advantage) with going it alone is that it doesn't require the approval of the Repub controlled House and Senate, thus bypassing the "impenetrable" blockade the Repubs put up around the White House.
That pretty much laid waste to the Repubs branding Obama as "the do nothing president" as well as infuriating the Repubs in Congress who tried their utmost to actually force him to be the "do nothing president" that they accused him of being yet failed in embarrassing fashion.
IMO, if it weren't for the Repub's strategy of total obstructionism, Obama would have had a lot more leverage against the health insurance companies when he and the Dems were cobbling together the ACA such that the program would have yielded much better results for the folks who really needed it and would have been much more affordable than it is now for everyone else.
As it was though, the Repub's opposition practically gave the health insurance industry the ability to virtually write themselves in as the prime beneficiaries of the program rather than the working class Americans it was meant to help.
Aside from that, the only problem I see that Obama had was that he was reaching across the aisle way too often and getting his fingernails pulled out every time he did it.
For a time those "agreements" that he and Harry Reid made with the Repubs invariably gave the Repubs "98% of what they wanted" thus short changing the middle class and the poor every time they shook hands.