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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast

Most landlords only think about insurance on renewal day—until a pipe bursts, a kitchen burns, or hail rips through a roof. That’s when the sequence of your next few moves can save you thousands or make a mess of your premiums and insurability.

In this Straight Up Chicago Investor Tuesday Tip, State Farm agent Josh Steigelmann joins Tom and Mark to break down the claim decision tree, what to do before you call anyone, how to protect your future underwriting, and what most investors get wrong about loss of rents, renters insurance, storm chasers, and documentation.

Whether you own a 3-flat or a 300-unit portfolio, this episode gives you a practical checklist you’ll want bookmarked.

Questions We Answer in This Episode

Q: Should landlords call the insurance company or the agent first after a loss?
A: Call your agent first. Claims hotlines must record and open a claim—even if you’re “just asking.” That can ding premiums and future insurability. Your agent can triage, advise, and keep you off the record until you decide.

Q: When is it worth filing an insurance claim vs. paying out of pocket?
A: Do the math: damage minus deductible vs. premium impact. Insurance is for catastrophic losses (fire, major water, full roof), not minor maintenance. If a $3k hail repair meets a $2.5k deductible, the $500 payout may be outweighed by multi-year premium increases—and it creates a claim on your record.

Q: How do claims affect multi-property owners with multiple LLCs?
A: Historically, claims were tied to the property/entity. Carriers are getting smarter. Today it should stay with the address/LLC, but expect more portfolio-level visibility over time. Plan accordingly.

Q: What should landlords do immediately after a covered loss (fire, burst pipe, etc.)?
A: Mitigate + Document. Stop ongoing damage, then photo/video everything, preserve physical evidence (e.g., the burst pipe), keep receipts, and start an itemized list. Don’t demo/finish repairs before the adjuster documents—unless required to mitigate further loss.

Q: How fast will an adjuster respond—and how do I get prioritized?
A: Typical outreach is 48–72 hours. In catastrophe surges, timelines slip. Flag severity up front (uninhabitable, displaced tenants) so your file gets triaged to the front.

Q: Who pays for hotels if a rental is uninhabitable—landlord or tenant?
A:

Landlord policy (Loss of Rents): Replaces rental income after approval.
Tenant’s renters policy (Loss of Use): Covers their hotel/temporary housing.
Pro tip: Require renters insurance and educate tenants before a crisis.

Q: Is Loss of Rents standard coverage on landlord policies?
A: Not always. Some carriers (like Josh’s) include 12 months by default with options to increase to 18–24 months. Verify your policy limits and waiting periods.

Q: Should I hire a public adjuster or let the carrier’s adjuster handle it?
A: Start with your agent + carrier adjuster. If the claim is complex or stalled, talk to your agent about next steps. Keep the adjuster an ally—cooperate, communicate, and provide clean documentation.

Q: How can landlords avoid roofing scams and contractor headaches?
A: Do not sign with storm chasers knocking on doors. Use reputable, insurance-savvy contractors who can produce detailed, line-item estimates (not “Roof: $20,000”). Your agent can refer trusted pros (no kickbacks allowed).

Q: Can tenant damage after move-out be an insurance claim?
A: Yes, if it’s vandalism or a sudden covered cause (e.g., intentionally left water running, holes punched, graffiti). Chronic neglect or long-term wear is not a claim. Diagnose the root cause (e.g., mold from prior roof damage is a path).

Show Notes

00:00 – Tuesday Tip intro; guest: Josh Steigelmann (State Farm)
00:50 – Call your agent first, not the 1-800 claim line; why “just asking” can open a claim
01:26 – Is it claim-worthy? Insurance is for catastrophes, not maintenance
02:49 – Deductibles vs. payout vs. future premium increases; hail/wind examples
04:27 – Apartment policy underwriting is tight—single small claims can hurt insurability
04:59 – Multiple LLCs: how a claim may (or may not) follow you across entities
06:12 – Legit claim playbook: mitigate, document, preserve evidence, then adjuster
08:12 – Adjuster timelines and how to get triaged when uninhabitable
09:14 – Loss of Rents (landlord) vs. Loss of Use (tenant renters policies)
10:05 – Some agents can issue advance checks for emergency needs—ask
11:29 – Start a contents list early; tenants should do the same (renters insurance)
12:24 – Is Loss of Rents included? Confirm limits and months (12/18/24)
13:38 – Case study: owner pays tenant hotels out of pocket—what should’ve happened
14:20 – Renters insurance is cheap (often ~$100/yr) and can be net-free with bundles
15:10 – Biggest mistake: storm chasers; why their contracts burn owners
16:19 – Use insurance-experienced contractors; submit line-item scopes/estimates
17:43 – Tenant move-out vandalism can be covered; investigate root cause for mold/water
19:33 – Build a relationship: “Have a guy”—your insurance agent is part of the team
20:03 – Chicago Fact: New Comiskey opening year trivia (answer: 1991)
21:26 – Outro: connect with the SUCI team

Takeaways for Chicago Property Managers and Landlords

Agent first, hotline second. Protect your record while you assess.
Claims are investments—underwrite them. Weigh payout vs. multi-year premium impact and insurability.
Mitigate and document. Photos, video, receipts, saved parts; don’t erase evidence before inspection.
Triage matters. If uninhabitable, say so—it moves you up the queue.
Loss of Rents is not a given. Confirm months and limits now, not during a fire.
Require renters insurance. It funds tenant lodging (Loss of Use) and reduces friction.
Avoid storm chasers. Use vetted, insurance-savvy contractors with line-item estimates.
Vandalism ≠ wear and tear. Intentional damage and sudden events are often covered.
Portfolio thinking. Even across LLCs, assume carriers will see the bigger picture soon.
Stay friendly with the adjuster. Cooperation speeds approvals and keeps options open.

Guest Name: Josh Steigelmann
Guest Company Website: https://www.statefarm.com/

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Dear Investor,

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