The current Prime Minister Patrick Manning of Trinidad and Tobago in a recent address to his nation placed the event in the local national as well as regional context:

My Friends, when we proposed that Trinidad and Tobago host two major international meetings at this time, we knew we were taking a giant step forward for our country and also for our CARICOM (Caribbean Community) partners. It was clear to us that our nation and our regional neighbourhood would emerge as a stronger voice in the community of nations. For far too long, smaller nations have existed on the global periphery; for far too long there has been mere tokenism in recognition of this reality; and for far too long countries and regions like ours have not had sufficient success in shaping an all-inclusive global agenda. If Trinidad and Tobago is aspiring to be a developed country, it must start to shoulder the commensurate responsibility. And so, here we are today.

Manning also took due note of the critical international context:

We should also recognise that the Fifth Summit of the Americas takes place during a crucial time in world affairs, when the issues to be discussed have become more important than ever and when the urgency for concrete collaborative action is even greater than in the past. The world is today facing an unprecedented economic crisis from which no country or region is insulated.

The financial crisis of the past several months affects us all. The entire world is now in a period of transition. Major economies now face weakening economic conditions with adverse consequences for social progress looming on the horizon. The current economic crisis could deepen existing vulnerabilities in our countries or expose new ones. The agreements reached at the Fifth Summit will take these developments into account.

At the same time, we must also recognize that the pillars of the Summit theme - human prosperity, energy security and environmental sustainability - are at the core of our ability to weather the financial storm capably and successfully.

Nevertheless, it is the US role in the region which inevitably draws attention.  What will be the new focus of the Obama Administration?  As Council of Foreign Relation's Nelson and David Rockefeller Senior Fellow for Latin American Studies, Dr. Julia Sweig reports:

For the first time in nearly two centuries, the United States will find a Latin America that has unapologetically dropped the region's traditional deference to U.S. power. When President Barack Obama and Secretary of State Hillary Clinton arrive for the Fifth Summit of the Americas in April, they will step into a political and diplomatic environment dramatically different from that confronting any of their predecessors. Understandably, the Obama administration will assert its disposition to forge partnerships, recover ground lost in recent years, and work toward the shared prosperity, social inclusion and common security agenda to which the region's governments have loosely agreed. But, with a global financial crisis and domestic recession constraining resources, not to mention a foreign-policy agenda that is all but saturated with other strategic priorities, the United States faces clear limitations on what it can achieve in its own neighborhood. Still, the forces of interdependence within the Americas remain as compelling as ever and require a strategy that advances U.S. interests in this new environment. As the countries of Latin America become stronger and more independent, the United States will face an uphill battle to make relationships work.

One of the things the United States apparently hopes will "bring it in from the cold" with regards to Latin America and the Caribbean is its openness to change in its relations with Cuba.  There has been speculation here at Daily Kos and elsewhere about recent changes instituted on that island nation that may point towards a new post-Castro era.  One might speculate that this could also be interpreted as a gesture toward the betterment of US-Cuban relations.  According to The Guardian,

President Barack Obama is poised to offer an olive branch to Cuba in an effort to repair the US's tattered reputation in Latin America.  The White House has moved to ease some travel and trade restrictions as a cautious first step towards better ties with Havana, raising hopes of an eventual lifting of the four-decade-old economic embargo. Several Bush-era controls are expected to be relaxed in the run-up to next month's Summit of the Americas in Trinidad and Tobago to gild the president's regional debut and signal a new era of "Yankee" cooperation. (...) "The effect on ordinary Cubans will be fairly significant. It will improve things and be very welcome," said a western diplomat in Havana. The changes would reverse hardline Bush policies but not fundamentally alter relations between the superpower and the island, he added. "It just takes us back to the 1990s."

Some are hopeful, while others are not so sanguine.  David Jessop of the Caribbean Council cautions:

Having spent much of the last week in Washington, it is clear that there is a need to manage Caribbean popular expectation downwards about the substance of the summit and to look more specifically at the ways in which subsequent meetings will determine how the region's future relationship with the United States will develop.
The US relationship is for the most part positive if low key. While there are contentious issues such as the future of offshore financial centres and other vital questions relating to security, Haiti, Cuba, migration, debt and trade, to say nothing of the global economic crisis, relations between the US and the nations of Cariforum are normal and unremarkable.

One thing is for sure.  As Peter Hakim, President of the Inter-American Dialogue, expressed:

Two things will make a difference in Port of Spain, however. First, Barack Obama, not George Bush, is now president of the US. Following the invasion of Iraq, Bush became a target of growing Latin American hostility; he represented what was widely perceived as Washington's unilateralism, militarism, and disregard for international rules and institutions--and its indifference to Latin America.  In contrast, Obama's election was enthusiastically welcomed in the region, and viewed as a hopeful sign of the vitality US democracy

We await the Spring thaw.