The direct challenges for Obama wrt Cuba are this:

1. A collapse of the Castro Regime would send tidal waves of destabilizing refugees (certain btw to vote Republican) to South Florida in a time of deep depression. The net result is the certain importation of future Republican voters, and a huge wave of resentment among current Americans, who would face new competition in a recession by new arrivals eager to work for much cheaper.

2. Propping up of Castro’s Regime leads to Republican gains in South Florida. It’s an easy win for Republicans.

3. Propping up of Castro’s Regime encourages more adventurism by Chavez, Fidel’s successor Raul, and Vladimir Putin. Perhaps even stationing of Russian nuclear missiles in Cuba and Venezuela. Ahem. This makes Obama a weak, ineffective, and dangerously naive-weak leader and Republican gains in Senate/House seats.

I submit Obama will once again vote … present. Do nothing, let events shape him and be caught up in the tidal wave of history. It’s likely that falling energy prices put a crimp in Putin and Chavez’s plans and aid to Cuba (mostly from cheap Venezuelan oil that Cuba resells). We are likely to see infighting among Cuba’s military, and a mass wave of refugees arriving in Key West and Miami totally inundating South Florida, and by the way transforming the state forever into a Cuba Norte province. A Mariel Boatlift times ten. With heavy fighting on the Island itself by military factions. Obama will dither and do nothing for as long as possible. Making people long for the decisive action of Bush during Katrina.

EVENTUALLY, events will force the US to intervene in Cuba, install a new regime, and urge (futilely) Cubans to return to Cuba. As a practical matter, Cuba will eventually become a US territory, and eventually a State.