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What Insurance Companies Don’t Tell Property Owners(Public Adjuster Explains)

By Tim Harstead - Friday, February 20, 2026

If You’re a Chicago Landlord or Real Estate Investor, This Episode Could Save You Thousands — or Even Millions

In Episode 6 of The Housing Providers Show, host Tim Harstead sits down with Dorian Bezanis of Alpha Adjusting to break down how insurance claims really work for rental property owners.

Many landlords misunderstand their policies — from 3% deductibles and coinsurance penalties to loss-of-rent coverage. This episode uncovers the hidden risks impacting Chicago multifamily owners, housing providers, and real estate investors.

Episode Breakdown

00:00 – Introduction of Dorian Bezanis
00:25 – What a public adjuster actually does
02:11 – Why you shouldn’t rely solely on the insurance company’s adjuster
05:50 – Staff adjusters vs. independent adjusters
08:06 – Are insurance companies using outdated pricing?
09:58 – Why relationships matter in insurance claims
12:33 – The appraisal process explained (insurance arbitration)
14:44 – Real-world loss-of-rent dispute example
16:46 – Loss of rent explained (NOT gross rent)
20:28 – Tenant renters insurance vs. landlord policy
24:39 – Why insurance claims take so long
26:02 – Surplus line carriers & shared-risk pools
28:16 – The future of property insurance
29:45 – How carriers are shifting risk to landlords
31:05 – Percentage deductibles explained (3% example)
34:42 – Biggest insurance mistakes landlords make
36:13 – Sewer backup, roof depreciation & code upgrades
40:07 – Coinsurance clause explained
42:26 – Underinsuring your property risk
44:28 – Investment regret & ownership lessons
46:14 – Long-term real estate mindset

Key Topics Covered

  • The 3% deductible trap (policy value vs. claim value)

  • Coinsurance clause explained for landlords

  • Loss of rent vs. gross rent (critical difference)

  • Why insurance claims take months to pay

  • Surplus lines insurance risks

  • Tenant insurance myths

  • Coverage gaps landlords should never skip

  • Replacement cost vs. market value for Chicago buildings

Whether you own a 2-flat, 3-flat, or multifamily property in Chicago, understanding insurance structure is essential in today’s rising premium environment.

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  • Chicago real estate investing

  • Property management strategies

  • Landlord protection

  • Housing provider education

#ChicagoLandlord #RealEstateInvesting #PropertyManagement #MultifamilyInvesting #LandlordTips

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Author

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Tim Harstead
Owns and operates Chicago Style Management, a full-service property management firm that operates on the south side of Chicago and specializes in C and D-class properties. Before getting into property management, Tim spent five years as a realtor helping investors find excellent properties, many years in construction, and several years in insurance as an agent, so he is well-versed in all the different departments needed when it comes to investing in real estate.
Owns and operates Chicago Style Management, a full-service property management firm that operates on the south side of Chicago and specializes in C and D-class properties. Before getting into property management, Tim spent five years as a realtor helping investors find excellent properties, many years in construction, and several years in insurance as an agent, so he is well-versed in all the different departments needed when it comes to investing in real estate.
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