At the same time, the organisation, representing candy titans Hershey, Mars and Jelly Belly, among other companies, is optimistic about scoring big, early policy wins from the Trump administration.
Among the industry's priorities: a long-sought rollback of government sugar subsidies that candy firms say drive up the costs of making their products.
"We have a very narrow window of time now with the current administration and political dynamics to win this fight," the group's president and chief executive, John Downs, wrote to the board of trustees in the days before this week's Doral meeting.
The memo, which was posted on the group's website, estimated that a victory on the sugar issue could save the industry $280 million annually.
Downs added that the group has "significant opportunities to go on offense" on other matters, including its push to end Obama-era regulations on genetically modified organisms (GMOs) and food labeling.
The group said it booked the venues in 2014 and 2015, long before Trump won the presidency.
And a spokesman said the sites were chosen for their locations and amenities, not in any effort to seek political favors.
But the arrangement illustrates a repercussion of Trump's decision to retain ownership of his business during his time in the White House - that he can become financially intertwined with a special interest that is simultaneously seeking to influence policy decisions by his administration.
By holding conferences at the Doral resort and the D.C. hotel, the confectioners group is making payments to businesses that directly benefit the president's personal fortune at the time the candy group is seeking policy changes in the administration.
In addition to the three events taking place during Trump's presidency, the group also held two conferences last year at Trump properties when he was running for office - a winter gathering in Doral and a September forum at the Washington, D.C., hotel.
The group declined to disclose how much it has paid the Trump company, but according to meeting planners familiar with the Trump Organization's prices, the price of the Doral events likely cost at least $100,000 to $200,000 each, not counting hotel rooms and extras such as spa services, while the D.C. hotel events likely run at least $100,000 apiece.
Ethics laws forbid executive branch officials to participate in government operations that could benefit them or their families.
Those restrictions do not apply to the president.
Trump's predecessors have typically abided by the same standard by putting their finances in blind trusts to avoid even the potential for a conflict, but Trump's aides have argued that such a setup would be impractical for a real estate company.
Ethics experts have previously raised concerns about Trump profiting from other events booked at his D.C. hotel, such as a recent event held by an association of railroad contractors and a gala scheduled for September by an association of college athletic directors forming a new political action committee.
A liberal watchdog group is suing Trump, claiming that some hotel events, such as a reception held last month by the Kuwaiti Embassy, violate a constitutional provision barring a president from taking payments or gifts from foreign governments.
The candymakers' association is the first known example of an interest group with multiple events planned at Trump properties during the Trump presidency.
Christopher Gindlesperger, spokesman for the confectioners, told The Washington Post that the conference sites are "completely unrelated" to the group's lobbying work.
"Our federal advocacy and regulatory agenda has remained the same as it has for years related to the sugar reform issue," he said.
"Anytime there is a new Congress or new administration there is a moment when the business community or other groups can tell their story about the jobs they can create, products they make, and the other contributions they make to the American economy."
Gindlesperger said the two Doral conferences were booked in 2014, while the three D.C. meetings were booked in 2015.
The venues, he said, were selected based on "the same criteria we always use: availability of lodging for a large group, quality of service, space to hold large meetings, and proximity to Capitol Hill."
A spokeswoman for the Trump Organization declined to comment for this report.
A White House official declined to be quoted by name but said that the White House counsel's office provides routine ethics training.
Trump announced shortly before taking office that he was removing himself from management of his company, a global real estate and branding enterprise that includes luxury hotels, golf courses, office buildings and merchandise.
His adult sons and a longtime executive are now running the company.
At the time, the lawyer who worked out the plan, Sheri Dillon, dismissed the suggestion of a problem resulting from "arms'-length transactions the president-elect has nothing to do with," such as hotel stays.
Nevertheless, addressing questions about potential violations of the Constitution's "emoluments clause," Dillon said, the company would donate to the US treasury "all profits from foreign government payments" to the Trump International Hotel.
Kathleen Clark, a Washington University law professor and ethics expert, said much is unknown about how White House officials are approaching potential conflicts related to business at Trump properties.
"I can envision a competition among interest groups to patronise Trump businesses, expanding the field of corrupt influence from one focused on contributions to campaigns, PACs and super-PACs, to one that includes enriching Trump businesses," she said.
In the case of the confectioners, Clark said, the group's chief rival in the sugar debate - the sugar-cane growers who support government price supports - may "reasonably believe that they are at a disadvantage."
"The sugar growers may feel pressure to even up the lobbying playing field by patronising Trump businesses," Clark said.
Phillip Hayes, a spokesman for the American Sugar Alliance, declined to speak in detail about the candymakers' decision to drive business to Trump's hotels.
But he used the opportunity to criticise the candymakers' group, which the sugar industry, often dubbed "Big Sugar" by critics, derides on its website as "Big Candy."
"I don't put anything past them," he said.
The candy association was one of the first major customers for the Trump International Hotel in the District.
The group took a leap of faith in the Trump Organisation by booking the September 2016 Washington Forum a year in advance, long before the hotel's completion.
At the time of the meeting, dozens of hotel rooms were not yet finished and construction crews were installing drywall and electrical systems.
The association, which funds a "CandyPAC," is making plans for an aggressive lobbying push over the next year, according to documents posted on its website.
The group plans to spend about $1.9 million on state and federal advocacy in 2017 to 2018, according to its business plan that was posted online. The document describes candy as "part of a happy and balanced lifestyle."
And it said the group's goal is to "enhance the positive perception of the industry through additional relationships with Congress, the administration and regulatory agencies."
Downs, the group's chief executive, wrote in his memo to trustees that he believes the Trump administration "should create a more favorable legislative/regulatory environment in Washington."
Strategic documents prepared for the Doral meeting also reveal how efforts targeted toward specific agencies within the Trump administration could affect the candymakers' bottom line.
The association wrote that it will be "closely watching" the upcoming confirmation process of agriculture secretary nominee Sonny Perdue, and that the group had worked with Senate staffers to shape questions for the former Georgia governor on a range of key issues.
That includes the candymakers' opposition to efforts by some states to prohibit candy purchases using food stamps, also known as the Supplemental Nutrition Assistance Program.
Documents laying out the National Confectioners Association's lobbying goals and other strategic materials were removed from the group's website over the weekend after The Post inquired about them.
