Wolf&Grayson EditorialAffordable housing operators know how to manage tight margins. But as premiums continue to climb, insurance has become a destabilizing line item. For portfolios built to preserve affordability, that volatility represents a strategic risk that can erode reserves, delay capital plans, and undermine long-term viability.
Kevin A. Weishaar, founder and executive coach at Weishaar Strategic Partners, has spent more than two decades inside multifamily operations, including affordable and market-rate housing across 21 states. He argues that operators who intend to stay viable must treat insurance as an operating discipline rather than a routine purchase. “One of the biggest things, which is tried and true, even though there’s some newer tools, is really around loss mitigation,” Weishaar says.
Rising costs are often framed as purely macro, driven by catastrophe losses, reinsurance pricing, or the broader hard market. Those forces matter, but they do not tell the full story for affordable housing. The market is increasingly granular, and insurers are looking for signals that differentiate risk. Owners who respond strategically are those who can demonstrate, in plain terms, how their assets perform and where exposures are actively managed. Loss mitigation sits at the center of that argument because it shows carriers what an operator is doing to prevent avoidable claims before they occur.
Insurance Is No Longer a Commodity Purchase
Water damage, fire, and liability events remain common drivers of loss. The most effective response, Weishaar says, blends operational fundamentals with targeted technology, such as IoT-enabled leak detection systems that automatically shut off water when sensors detect sudden changes. Those tools work best when paired with “having a good preventative maintenance plan.” Even established safeguards, such as stove-top shutoffs, continue to play an important role in a comprehensive risk strategy.
The differentiator is not just the interventions, but the way they are documented and presented. “Being proactive about documenting that stuff and presenting it to your brokers, or some of the bigger providers, to say we’ve got a thoughtful approach to loss mitigation,” explains Weishaar, “Is really the best approach to being able to save money in the long run on your insurance.”
Don’t Get “Lumped In” With Risk You Don’t Have
Even when operators invest in loss mitigation and documentation, insurers often price affordable housing as if it were a single risk category. That oversimplification has become one of the most damaging dynamics in today’s market. “The tendency [is] to statistically lump all of affordable housing together,” he says.
Much of the severe loss experience clusters at one end of the spectrum, particularly “permanent supportive housing” and other forms of transitional or homeless housing in urban core cities. Those properties often face higher incidences of crime, pests, and damage from water or fire, all of which can drive claims frequency and severity.
By contrast, other segments carry a meaningfully different risk profile, such as senior housing, rural development, or portfolios dominated by 60% tax credit properties, which often serve households with more stable income profiles and lower volatility. Yet many providers are still “profiled in that way” as if they sit in the highest-risk tier. Weishaar isn’t suggesting insurers are acting irrationally, because carriers have to cover losses somehow, but operators have agency in how their own data is framed.
The path forward begins with separating the portfolio narrative from the category label. Loss runs are foundational. Where possible, operators can segregate properties by location and exposure, and use external indicators such as crime statistics to clarify differences among assets to show which risks are present, which are not, and what has been done to reduce the ones that are.
Build an Underwriting-Ready Story With Your Broker
The right broker matters, and the best operators prepare a case rather than hoping underwriters will discover nuance on their own. “If you can make the case, if you can find the right broker… loss runs is the first,” he says. Resident profile summaries, stabilized occupancy trends, and clear data that reflects how a property is actually operated should follow close behind.
That case needs to be specific. Strong track records should be attached to specific properties and timeframes. If a portfolio includes mixed risk levels, separating assets into distinct underwriting narratives can keep the stronger performers from subsidizing the weakest. Operators can also bring context that insurers may not readily understand, especially around resident qualification.
Weishaar offers an example from recent work he did in Washington state. In King and Snohomish counties, area median income can be around $120,000. That matters because a 60% tax credit household can be closer to six figures than many people expect. The challenge is that those realities can be difficult to communicate to audiences that equate “affordable” with a single socioeconomic profile. “It’s a more nuanced conversation,” he says.
Use Loss Mitigation Experts Like a Field Strategy Team
Premiums are influenced by more than claims history. Building construction, site conditions, and property-specific vulnerabilities all shape how insurers price a risk, which is why Weishaar urges operators to get close to the people who understand those details and can turn improvements into premium impact.
“Be best friends with the loss mitigation expert, with your insurance broker or company,” he says. “Have them walk your properties and they’ll be able to tell you: what are some of the things that are unique to your property that could help you bring your costs down.”
For example, on a recent project, a property walkthrough revealed that a first-floor slider door configuration had a door jamb that made break-ins easier. The recommendation was to replace the existing screws with larger ones to reduce forced entries. The value was not just the fix itself, but the ability for the loss mitigation specialist to “go back and talk about this” with carriers as a concrete, documented risk-reduction measure.
These walkthroughs can surface similar opportunities: targeted security upgrades, changes to lighting and access control, water shutoff enhancements, or adjustments to maintenance practices that reduce claim-prone failures. The common thread is follow-through, including photographs, invoices, and implementation timelines that make the improvements real to an underwriter.
Data and AI Will Reward the Operators Who Can Aim It
Insurers are becoming more data-driven, and Weishaar expects them to move faster than property managers. “They’re going to be out in front on data probably quicker and better than the property management world,” he says. “They’re going to like their data better than our data for sure.”
That imbalance is a warning and an opportunity. As underwriting models become more automated, operators who do not supply credible, structured information may be evaluated on proxy indicators that do not reflect their real risk. But when operators can shape the inputs, AI could also help distinguish the segments that are currently being priced as one.
Weishaar sees promise in using AI to illuminate what veteran operators often know intuitively but struggle to prove at scale. “What’s my intuition of having done hundreds and hundreds of those properties is that it is a lower risk profile, but I can’t prove it,” he says, referring to certain rural development assets. “If you take the entire national portfolio of USDA RD properties, you’d be able to demonstrate it.”
Why Learning Insurance Is Now a Leadership Skill
The implications go beyond renewal negotiations. Insurance touches capital planning, lender requirements, and the feasibility of keeping rents affordable while maintaining safe, well-run properties. As the market becomes more analytical, the operators who treat insurance literacy as part of leadership will be better positioned to protect both mission and margin.
“Get comfortable with learning insurance,” Weishaar says. Early in his career, that meant reading policies and exclusions line by line. Today, AI can speed the work, allowing teams to surface exclusions, coverage gaps, and structural weaknesses faster. The responsibility still sits with leadership. Insurance is no longer a passive expense. It is a strategic lever.
Follow Kevin A. Weishaar on LinkedIn or visit his website for more insights.
