This year's meeting is significant because the majority of OAS members seem determined on repealing the 1962 resolution which effectively suspended Cuba's membership. Many countries in Latin America now favor Cuba's possible re-entry into the OAS, and U.S. policy towards Cuba seems to be an obstacle in exercising this effort.
While some analysts agree that the 1962 OAS resolution should be rescinded, others, like Sec. Clinton, feel that conditions should be attached beforehand. There is also the possibility that an agreement will not be reached by the OAS this week, but a dialogue (with the help of Brazil) might extend over into next year.
I personally agree wholeheartedly with the position of John McAuliff of the Fund for Reconciliation and Development. His recent post at the Havana Note makes perfect sense:
"Placing special conditions on Cuba’s membership or ducking the issue brands the organization as still too compliant with US domestic political agendas and sustains Fidel Castro’s anti-OAS argument. An extended dialogue about reentry is likely given Cuba’s oft repeated denunciation of the OAS, but such a very useful process can only begin if the 1962 suspension is repealed and it is only up to Cuba to decide if and when it retakes its seat.
"As with the rest of [U.S.-Cuba] policy to date, trying to maintain leverage by incremental change is living in denial and counterproductive. Secretary Clinton should simply abstain if the OAS votes on ending Cuba's suspension without conditions. In that way she demonstrates we are listening and serious about a new collaborative role, even if the Administration is not able politically to join the affirmative vote."
[Additional analysis at the Cuban Triangle blog.]