(Cross posted on http://laredcubana.blogspot.com/)
The obstacles are political, not technical.
Eric Schmidt and other Google executives traveled to Cuba where they met with members of the Internet community and the government. Google is providing Internet access in a few US Cities and is considering others -- might they provide Internet access in Cuba?
Consider the following:
But, the Cuban government has feared the Internet since the time of their first IP connectivity in 1996. At that time, there was high level debate about the Internet. The hard liners, led by Raúl Castro, argued against the Internet while others argued for a "Chinese" approach of supporting Internet use while censoring content and surveilling users. (It seems Fidel Castro was ambivalent).
The hard liners won in 1996, but what about today? Schmidt reports that a "number of the people" he spoke with said "the eventual model of Cuba would be more like China or Vietnam than of Venezuela or Mexico." If some of those were young government officials, there may be a glimmer of hope.
Update, July 3, 2014
It is noteworthy that Jared Cohen, Google's Director of Ideas, accompanied Schmidt on this trip -- before joining Google, he was a member of the Secretary of State's Policy Planning Staff and served as an advisor to Condoleezza Rice and later Hillary Clinton.