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Cuba's President Raul Castro greets members of the National Assembly at the start of a session in Havana, December 20, 2014. Castro says the U.S. should respect Cuba’s communist system as the two countries work to restore relations.STRINGER/Reuters

Measuring Stephen Harper's success or failure at this weekend's meeting of hemispheric leaders in Panama will depend on how he navigates a complex collection of thorny issues across the Americas, experts say.

Harper could face challenges stickhandling two major topics that are expected to attract much of the attention during the two-day Summit of the Americas: the deepening crisis in Venezuela and the warming relationship between the United States and communist Cuba.

The prime minister arrived in Panama City on Friday for the summit, which is expected to be overshadowed by the historic encounter between the U.S. and Cuban presidents as the countries work to normalize diplomatic relations.

But not only will Harper, who has been critical of the Cuban regime in the past, have to position himself on the rapprochement, he may find himself weighing in on the troubles in Venezuela and its dispute with the U.S.

The Obama administration recently levied sanctions against seven Venezuelan government officials to put pressure on President Nicolas Maduro's crackdown on his political opponents. Obama's executive order described Venezuela as a security threat to U.S., which Maduro and his allies called an act of aggression.

"(The U.S. move) has been roundly condemned by all Latin American countries, including countries that are very close to the United States," said Jean Daudelin, a Carleton University professor who specializes in development and Latin America.

Daudelin said summit members might produce a resolution over the weekend that denounces the U.S. for its sanctions and rhetoric against the Venezuelans.

He believes it could create significant divisions among the 30-odd member states.

Success for Canada, Daudelin said, might be dodging the sanctions dispute, while instead focusing on simply applying pressure on Venezuela to become more democratic.

"I expect Canada to be one of the most-forceful critics of Venezuela," he said, adding that while many countries would oppose that position, he doesn't think it would have major consequences on Canada.

When it comes to Venezuela's close ally Cuba, Harper has had strong words for the Castro regime — and communism in general — in the past and he had initially opposed its invitation to this summit.

Harper has been much more critical of Cuba than past prime ministers, Daudelin said.

But in Panama, Harper would welcome an opportunity to meet Cuban President Raul Castro, a government source has said.

Ottawa, the source added, is "very pleased" with the direction Cuba is headed, though it remains "deeply concerned" with the country's human rights record.

Harper will also seek to use the summit as a way to meet the government's objectives for the hemisphere, such as promoting human rights, security and prosperity.

The government announced $98.1 million worth of "economic" projects Friday in Cuba, Honduras, Colombia, Peru and Guatemala. The investments will focus on areas such as rural economic development, small-scale mining, sustainable food production and youth entrepreneurship.

Harper is scheduled attend a meeting Friday with several business leaders at a CEOs gathering connected to the Summit of the Americas.

Canada has considerable business ties in the Americas, including free-trade agreements with eight countries.

The Harper government has long touted its trade credentials, but Daudelin doesn't see a lot of opportunity for any gains at the summit, especially since he said there's been little progress with big economies of Brazil and Argentina.

"All the well-functioning economies of Latin America have free-trade agreements with Canada and the United States," he said.

Latin American expert Carlo Dade said the Summit of the Americas isn't the best venue for Harper to talk a lot about trade. He would be better off saving those discussions for talks with members of the Pacific Alliance, such as emerging economy of Colombia.

At one time it was important, but we now go to the Summit of the Americas because we have to, Dade said.

"It's like the annual meeting or conference for certified accountants or construction companies," said Dade, director of trade and investment policy for The Canada West Foundation.

"You go because it's your business, your peers are there, you network, you cannot not go."