Just to bring up a random hobby horse: The botched implementation of electronic medical records - which remain expensive, laborious to implement, difficult to use, and in many cases unable to communicate with each other - is one of the biggest domestic policy missteps of Obama's presidency, yet hardly anyone who works outside of health care talks about it.
My mother worked at a hospital for awhile and was in charge of this process for her particular office. She basically described the transition as a total nightmare. Incredibly time consuming, required far more training to navigate, almost completely pointless in the long run, and whenever there was any issue with the computer system, which was a fairly common occurrence, all records just got stuck in the ether. I never understood it.