Corey
Yes, both sides should benefit. The beauty of free trade is it's not a zero sum game. Whether Cuba benefits more in percentage or even absolute terms doesn't matter. What matters is whether the U.S. sees a net marginal benefit over its prior policy. I think we will, you don't, we just have to agree to disagree and see how things play out.
The designation of Cuba as a rogue state is particular to the U.S. Fair enough, but by international norms Cuba fails to meet the criteria, thus the US has stood virtually alone in its embargo. Juxtaposing Cuba with the DPRK does a great job of illustrating why the latter meets the criteria and the former fails.
You appear to be making the argument the DPRK might take lessons from our change in policy wrt Cuba. I certainly hope so! For starters, stop threatening the world, sign the NNPT and join the global community.