There were not many things I agreed with Obama on. The 2016 deal that reopened at least some trade with Cuba was one of them. Communism makes people poor and capitalism makes them wealthy. It really is that simple.
I have no idea how President-elect Trump will handle relations with Cuba, but as a libertarian I hope he works some of that "Art Of The Deal" magic to keep goods flowing to and from the island.
From 2014, a Rand Paul opinion piece in Time magazine titled Cuba Isolationists Just Don't Get It lays out the perfect case:
I support engagement, diplomacy, and trade with Cuba, China, Vietnam, and many countries with less than stellar human rights records, because I believe that once enslaved people taste freedom and see the products of capitalism they will become hungry for freedom themselves.
President George W. Bush wrote that “trade creates the habits of freedom,” and trade provides the seeds of freedom that begin “to create the expectations of democracy.” Once trade begins it is hard to hide the amazing products of capitalism. The Soviets used to produce documentaries depicting poverty in America but it backfired when Russian viewers noticed that even in the poorest of circumstances you could still see televisions flickering in the windows. Once trade is enhanced with Cuba, it will be impossible to hide the bounty that freedom provides.