Obama made the mistake of assuming that the GOP would actually work in good faith with him on critical issues to get at least something for themselves rather than just trying to block everything. Pretty much every flaw of the Affordable Care Act comes from including Republican proposals in a vain bid to get their support instead of just making the best bill from the start.
I'd like to think that future Presidents will remember that.
Don't forget that Congressional Democrats were afraid to get off their asses and use their control of both legislative and executive branches to effect some real change. They had control for two years and were more concerned with straddling the middle in hopes of re-election only to be ousted anyway in the Tea Party election of 2010.