Despite the demise of Fidel Castro, I don't think Trump will open up diplomatic and trade relations with Cuba. How will living conditions in Cuba improve if the world does not trade with them? All this talk of protectionism and reducing trade really harms the majority of the populations of the world. Now, only if all our world leaders, including Raul Castro and Trump, could understand that.
The Trump administration will roll back Obama's easing of trade barriers to Cuban exports. Traditional, conservative administrations have worked harder to place strict barriers and bans between the United States and Cuba. This may be affected by Fidel Castro's recent death, but Cuba will likely continue under a form of dictatorship. Trump will most likely work to replace the trade barriers to Cuban exports.
Yes, the Trump Administration will roll back Obama's easing of trade barriers to Cuban exports. Donald Trump campaigned on a platform of extreme protectionism in regards to trade policy and has taken actions since being elected to suggest he will continue this philosoophy. It is also worth noting that Republicans are incredibly antagonistic toward Cuba due to differences in political ideology.
Trump is a businessman. He knows what works and what doesn't. Trump knows that trade barriers don't work. Cuba's new leader is more liberal and open to a relationship with the United States than Fidel was. Trump knows that it doesn't make any sense to work backwards. He will open new trade with Cuba.