At the National Apartment Association's Apartmentalize conference in New Orleans on June 17, multifamily operators detailed how they are using artificial intelligence to produce weekly property reports with actionable insights, draft resident letters, and prepare for difficult conversations with residents and team members. The panelists also warned that employees experimenting with AI must guard against oversharing sensitive data, after one firm learned that a lender had discovered its private rent roll and operating statement inside a free AI tool.
Anne Hollander, vice president of AI and innovation at WinnCompanies, described a case from a few years ago where an employee put a property's financial information into ChatGPT. "We had a case a few years ago now where a lender was basically using ChatGPT, kind of like a Google search, and looking down the list of assets that they had to see if there was any information that they found," Hollander said. "One of the assets popped up a rent roll, an operating statement, a trial balance - all coming back out to this person - that was accurate based on the data that they were looking at." The lender also noticed discrepancies with the reporting the property management firm had been providing. "What do you think happened with that property manager," Hollander said. "That was probably not a fun phone call [with the lender]."
Despite such missteps, the practical uses of AI in property operations are growing. The approaches shared at Apartmentalize show how AI for Real Estate & Construction is moving from experimentation into daily workflows.
Providing weekly reports
Jessica Dakin, vice president of performance strategy at BH Management, said the company hit an inflection point around 2023 or 2024 as teams got leaner and clients demanded more. "Our clients were asking for more reporting faster, more data faster, more insights faster," Dakin said. "What are you going to do about the evolving industry? And we knew we had to pull [up] our sleeves and do something about it." BH Management formed a specialist group to explore AI's potential. That work led to a weekly report that generates property-level insights across the firm's national portfolio. The report answers questions about market performance and guides associates' focus. "They know exactly where their focus should be and they know exactly what changed week over week," Dakin said.
Writing letters to residents
Not every firm has the scale for weekly automated reports, but onsite teams can still adopt AI for routine tasks. WinnCompanies uses a company-licensed tool that pulls in templates, policies, and procedures to draft resident letters. "When I hit enter, it's going to think a little bit when you pull that information together and, in a matter of a few seconds, generate back out what that letter should be from there," Hollander said. The system asks whether the output should be an email, a printed document, or a resident portal post, and employees can edit the result in real time. "I can like the response if it's great, I can copy it directly and I can even say, 'Nope, it's not good enough for me,'" Hollander said.
Preparing for difficult discussions
When noise violations or sensitive issues require in-person conversations, AI can help staff prepare. Crystal O'Brien, vice president of human resources at WinnCompanies, recalled spending hours years ago scripting what to say to a resident who treated swimwear as optional at the community pool. "If I would have had AI, it would have gotten so much faster," O'Brien said. The same approach works for tough talks with team members. "I can tell it that I'm having a difficult conversation with this team member, help draft, help me with some talking points, and it will do the same sort of thing," O'Brien said.
Why this matters for management
For managers overseeing property operations, these examples show AI is not just a back-office experiment. It is being used to shrink the time between data collection and decision-making, to standardize resident communications, and to give team members a starting point for awkward conversations. The key is pairing AI adoption with clear data-sharing policies so that the efficiency gains do not come with a compliance risk. Managers who define what information can safely enter a prompt will get more out of the technology while avoiding the kind of lender phone call that no one wants to take.
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