In Vancouver, the developer of a new Trump Tower has been under pressure for months to drop the Republican presidential candidate's name from the project. Meanwhile, the Trump Tower in Toronto is the subject of a lawsuit after facing years of controversy.
Donald Trump's controversial run for US president is having an impact on his businesses in Canada and knock-on effects for those who have partnered with his brand.
The opening date for the Vancouver hotel has been delayed until 2017, well after November's US election. A contest offering a chance to meet with the Trump family for the grand opening caused a stir.
Across the country, the Toronto building, which opened in 2012, has been the target of a lawsuit by small investors who claim they were misled into buying into the project. Its developer, Talon Development Inc, has tried to remove the Trump name from the troubled hotel and condominium complex.
Brent Toderian, a Vancouver-based city planner, was the first to openly oppose Trump branding on the 63-storey Canadian tower, designed by famed architect Arthur Erickson to have a distinctive 45-degree twist as it rose into the sky.
"We've taken a building that is the second-tallest in the skyline, carefully planned at least in part by one of our most revered Canadian architects - a very elegant piece of architecture for our skyline - and retroactively duct-taped Trump's name to it," he said in an interview.
The luxury hotel and condominium tower in downtown Vancouver is owned by the Holborn Group, a private real-estate developer which partnered with the Trump brand in 2013.
Mr Trump attended the announcement, accompanied by his children, Eric, Ivanka, and Donald Jr.
"I believe it's going to be a fantastic success. I love Vancouver," said Mr Trump at the time.
The project is licensed to use the Trump name and brand - including for Canada's first Mar-a-Lago Spa by Ivanka Trump - and will be managed by the real estate magnate's company, which is also overseeing the building's interior design.
In December, Mr Toderian renewed his call for the Holborn Group to distance themselves from the Trump name. He was joined by Vancouver Mayor Gregor Robertson, who said the brand had no place on the city's skyline.
"Donald Trump's hateful positions and commentary remind us all of much darker times in our world's past - and it is incumbent upon all of us to forcefully challenge hatred in all of the ways that it confronts us," he wrote in a letter to the developer.
The Holborn Group did not respond to requests for comment but in previous statements has noted that the still-unfinished building will create some 300 new jobs.
"Holborn, a company that has contributed immensely to the growth of Vancouver, is not in any way involved in US politics. As such, we would not comment further on Mr Trump's personal or political agenda, nor any political issues, local or foreign,"CEO Joo Kim Tiah said in December.
In Toronto, project developer Talon was close to a deal to sell the troubled 65-storey hotel and condominium complex at the heart of the city's financial district earlier this year. However, Toronto's Trump Tower is currently off the market.
Talon chairman Alex Shnaider was also trying to have the Trump name removed from the building, at one point seeking to do so through arbitration. Those efforts also appear to have stalled. A lawyer for Talon refused to comment other than to note there is currently no lawsuit between the owners of the hotel and Mr Trump.
Mr Trump first announced his involvement in an early version of the project in 2001 and it was brought under the Trump brand umbrella in 2004. The businessman attended the official groundbreaking in 2007.
The Trump Organization does not have an ownership stake in the building but it operates and manages the hotel and licenses the Trump name to the complex for a fee.
The building is the subject of a lawsuit by disgruntled buyers who lost money after investing in the property, in one instance almost 1m Canadian dollars ($750,000; £613,000).
In a recent decision, an Ontario court ruled in favour of two investors, saying one could be discharged from his obligations and another could be awarded damages.
Talon is considering appealing against the decision.