In this episode of The Property Playbook, Peter Carlseen sits down with Drake and Denise Dawley of My New Leaf Insurance to discuss why insurance has become a major concern for landlords and homeowners. Denise shares that their entry into the insurance industry was sparked by a personal experience: her parents suffered water damage that wasn’t covered due to a policy exclusion they didn’t understand. That moment highlighted how confusing insurance policies can be and motivated her to focus on educating clients, eliminating gray areas, and making sure people truly understand what is—and isn’t—covered before a loss occurs.

The conversation emphasizes common insurance pitfalls, especially for landlords. The Dollies stress the importance of calling your insurance broker—not the carrier—before opening a claim, since even zero-payout claims can negatively affect future insurability. They explain why having the cheapest policy is often risky, noting widespread underinsurance and rising rebuild costs. For landlords in particular, proper landlord policies, sufficient liability coverage, umbrella policies, and higher deductibles paired with savings strategies can reduce long-term risk while keeping premiums manageable. They also discuss how claims, property condition, roof age, brush clearance, and even drones and aerial inspections now heavily influence insurability.

The episode also explores the broader challenges of today’s insurance market, including carriers pulling back from California, moratoriums during fire events, rising premiums, and stricter underwriting standards. Drake and Denise advise landlords to secure insurance early during escrow, avoid policy lapses, regularly review coverage, and document personal property through photos or videos. Their core message is proactive planning: understand your policy, shop thoughtfully, maintain your property, and work with a broker who prioritizes proper coverage over price—because insurance only proves its value when something goes wrong.

Got a rental property? Find out why hundreds of landlords have trusted Praecelsus Property Management, Inc with their investment properties.

You can learn more at www.PraeHomes.com or better yet, contact Peter Carlseen directly for a free consultation at 877-772-3466 or info@praehomes.com

If you're in San Diego County, chances are, we can help you! And if you're property is located anywhere else in the world, we can get you connected through our established network of trusted professionals.

In the meantime, hit LIKE and SUBSCRIBE and be sure to listed to all of our episodes!