The most significant error in judgement by the Obama Administration and the government of the Republic of Cuba: believing the time-frame for opportunity was 17 December 2014 to 20 January 2017 (inauguration day) rather than 17 December 2014 to 8 November 2016 (election day).
The government of the Republic of Cuba did not believe that Donald Trump would win. The Obama Administration did not believe that Hillary Clinton would lose. They each planned poorly.
The governments have focused upon what was easy rather than what was difficult in part because each believed there would be continuity.
During the last twenty-four months, there have been opportunities missed, abandoned, and mishandled. The difficult issues have been avoided by both governments- and the United States business community has suffered for it.