In the latest issue of Military Review, a main journal of the U.S. Army, I have an article co-authored with a Latin American Studies graduate student on U.S. policy options for a Cuban Spring. We discuss both the legislation and official policy (both toward Cuba and general) currently in place, and further put it in the context of the Arab Spring.
The upshot: in the event of regime change in Cuba, the U.S. has a constructive role to play, but engagement should multilateral and non-military. Otherwise it would be counterproductive both for U.S. policy and for Cuban democracy:
The history of U.S.-Cuba relations and the experience of the Arab Spring provide a useful context for identifying the optimal policy responses to an eventual Cuban political transition. There is a fine line between caution and passivity, but this line is one the United States must walk. There will be strong resistance to a foreign presence, and the possibility of blowback is very real. The United States can and must play a role in Cuban democratization, but it cannot create it.
Gregory Weeks and Erin Fiorey, "Policy Options for a Cuban Spring." Military Review May-June 2012: 88-95.