1) Latin American Left: the Pink Tide: 1999-present?
Two recent pieces on the status and prospects of the progressive governments, social movements and multilateral institutions collectively known as the ‘Pink Tide’.
Raúl Zibechi: Taking stock of ‘Progresismo’ in Latin America [source]
Immanuel Wallerstein: The Latin American Left Moves Rightward [source]
(NB I have the utmost respect for both these writers, but the optimist in me has to say that it is surely too early to mark the high water of the ‘Pink Tide’.)

2) Upcoming elections:

Argentina: Presidential, Second Round.
The Kirchners have been in power 12 years and have left a legacy of “trade protectionism, social welfare and defence of the working class”.
Pre first round introduction to candidates:
Argentina: The End or a New Path for Kirchernismo? [source]
Post-first round analysis of the 2 candidates to contest the second round in November:
Argentine presidential run-off in November but with completely different scenario [source]

Venezuela: Mid Term.
First and foremost of the ‘Pink Tide’, Venezuelan Bolivarianism, in alliance with the Cuban Revolution, is the trail blazer of the Latin American progressive project. The transition to a ‘post-Chavez Chavismo’ under Nicolas Maduro has been marked by a wide variety of destabilization from foreign-backed opposition forces:
This article high-lights the historic high level of female and youth candidates but also warns of the threat of opposition violence in the upcoming midterm elections:
Peace at Stake in Venezuela’s Upcoming Assembly Elections [source]
This article quotes polls showing the PSUV, of the Chavista President Maduro, ahead in voting intentions:
Maduro Makes Moves toward Economic Reform as New Poll Predicts PSUV Win [source]

3) Developments and Context:

Brazil:
Since 2003 Brazil has seen a remarkable transformation due to good economic growth and political leadership within Latin America and on the World stage through organizations such MERCOSUR and BRICS. This has been achieved with progressives at the helm, firstly Lula da Silva, but also his successor Dilma Rousseff. Presidents can serve only 2 terms in Brazil, and Rousseff won her second before a corruption scandal decimated her authority.

This article gives evidence that Rousseff has moved to the right in order to head off impeachment attempts:
The United States Wins In Brazil, Raul Zibechi [source]

Mexico
The disappearance of the 43 students one year ago lead to a marked increase in protest to the ongoing drug fuelled violence in Mexico, which began under the previous President Felipe Calderon and continues under Enrique Peña Nieto. This article assesses the dramatic repercussions of the event a year on.
Ayotzinapa, State Violence and Terror By Laura Carlsen [source]

Nicaragua
Russia joins China in the construction of an alternative to the US dominated Panama canal in Nicaragua, a member of the radical progressive block ALBA.
Russia Interested in Joining the Nicaragua Canal Project (Sputnik – Russian news agency)

Guatemala
Political new-comer wins Guatemalan Presidential elections in the aftermath of wide spread protests that brought down the previous government in the most populous Central American state:
Comedian cowboy who wanted to become president, finally makes it in Guatemala [source]

Cuba:
The US isolated on World Stage:
World Discusses the Blockade on Cuba at the UN [source]

Peru:
Ollanta Humala, who defeated right-wing candidate to win the 6-year Presidency in 2011 on a progressive ticket, has seen his approval drop to 12% and faces increasing protest, presumably due to him quickly tacking to the right after his election victory.
Act of Treason: Secret US Sites in Peru Nil NIKANDROV | 13.10.2015 | [source]

Bolivia:
Evo Morales, first indigenous President of in the Americas, marks 10 years in power. Bolivia is a key member of the radical progressive alliance ALBA.
10 Years of Evo Morales, Telesur. [source]