Insurance has become a frequent obstacle in Florida real estate transactions. Still, one agent argues that deals collapse mainly when agents fail to anticipate and address insurance issues early, rather than because insurance is inherently unmanageable.
“It’s easy for a deal to fall apart because of insurance if you don’t know what you’re doing,” says Zach DiFilippo, a Realtor with Coldwell Banker Premier Properties in St. Augustine. DiFilippo attributes his success to a strong working relationship with insurance specialist Ryan Flagler of Bright Way Insurance. “I am absolutely blessed because of the relationships that I have in that world. I work with a guy, Ryan Flagler, with Bright Way Insurance, who is a wizard when it comes to that.”
DiFilippo says the difference between smooth closings and last-minute crises often comes down to whether agents have educated themselves about insurance requirements and have reliable experts to consult before buyers make offers. “I’ve been educated enough by him through experience, his experience, and then the deals that I’ve done with him that I’m able to kind of see around the corner when it comes to certain deals so that there isn’t any surprises,” he explains.
DiFilippo’s process involves addressing insurance as part of a buyer’s due diligence—before an offer is made—rather than waiting until a contract is signed. This ensures buyers know the actual cost of ownership, including insurance premiums that may be far higher than expected, before making financial decisions.
“Insurance is a hot topic. But if you know what you’re doing ahead of time, you can kind of set that expectation before it blows up,” DiFilippo says. He notes that while inspections can still uncover some issues, insurance factors that agents could have identified earlier drive most surprise costs and last-minute renegotiations.
This approach requires agents to help buyers evaluate key factors influencing insurance costs and availability: roof age, proximity to the coast, prior claims history, and construction materials. DiFilippo warns that agents who ignore insurance or fail to involve knowledgeable specialists expose their clients to unnecessary risks and failed deals.
Despite detailed planning, DiFilippo acknowledges that unexpected insurance issues can still arise during a transaction. “You don’t know everything. Things can come up at the last minute, or there might be something that comes up on the inspection,” he says. When this happens, the outcome depends on the motivation and flexibility of both buyer and seller.
“That’s when the motivation of the buyer and seller, how much they’re willing to negotiate, kicks in,” he explains. In situations where buyers and sellers are motivated by pressing factors—such as job relocations, family needs, or time constraints—they are more likely to negotiate solutions to insurance challenges. In less urgent transactions, insurance problems are more likely to end deals.
DiFilippo observes that insurance complications are most likely to derail sales when buyers lack strong motivation or sellers maintain unrealistic expectations about the market. When both sides have clear reasons to close, insurance becomes a hurdle to overcome rather than a deal-breaker.
DiFilippo credits his relationship with an experienced insurance specialist as a key advantage. By working closely with someone who understands the nuances of the local insurance market, he can offer clients guidance beyond what generic online quotes or less experienced agents provide.
This collaborative approach marks a shift from treating insurance as an afterthought to making it a central part of the agent’s advisory role. DiFilippo argues that agents who fail to develop insurance expertise or relationships put their clients at risk for avoidable surprises and failed transactions.
Whether DiFilippo’s methods become the norm in Florida will likely depend on how many deals continue to unravel over insurance in the coming months. With insurance costs rising and carrier options tightening, agents who can’t help clients navigate these obstacles may lose business to those who can.
For now, DiFilippo’s main takeaway is clear: insurance rarely derails deals when agents do their homework and set realistic expectations before buyers commit. Most failed transactions, he says, result from professionals neglecting insurance until it’s too late, not from truly unsolvable insurance problems.
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