I thought we should have opened up years ago to Cuba, even when they were at their most totalitarian. After all, 60 years is probably enough time to prove sanctions are not enough to bring Cuban leadership to their knees, and in the intervening time we have seen any number of examples of the power of trade and open interaction helping to topple bad regimes.
Unfortunately, I think we have been prevented in doing so by pure ego (we don't want to admit a failed policy we put so much bipartisan effort into) as well as Florida electoral politics (anti-Castro votes considered swing votes in a swing state). I don't know what to do about the latter -- we have ethanol subsidies for the same reason (ie Iowa's prominence in the presidential selection process). However, with Cuba currently mitigating some of its worst socialist impulses, it strikes me that now is the time we can overcome the ego problem and simply declare victory. Unfortunately, we now have a President that may want to continue punishing Cuba, this time for lowering taxes and reducing the size of government.