A damaged home after a large tree fell on it.
If you have ever filed a homeowners insurance claim, you know it can feel more like an endurance test than a straightforward process. The savvy financial advisor Rick Kahler, president of Kahler Financial Group in Rapid City, S. D., tells us how to navigate this treacherous path.
Larry Light: Trying to get paid for damage to your dwelling sounds like torture.
Rick Kahler: While insurers are legally required to honor valid claims, they have strong financial incentives to delay, underpay or deny them whenever possible.
Over the years, I’ve learned this the hard way. The most recent lesson started when a hailstorm hit my home in June 2023. I promptly filed an insurance claim. I relied on a roofing contractor to handle the whole claim, including the gutter and siding damage. That was my first mistake.
About 15 months later, my roof and gutters were replaced, but the siding repairs and painting remained undone. Every time the insurance company reassigned my claim to a new adjuster, I had to start over. When I called the contractor after a period of inactivity, they said the adjuster had ghosted them, so they’d given up—and I still owed them the full roofing bill.
Light: What did you do then?
Kahler: At that point, I had two choices: pay out of pocket for the unfinished work or escalate. I chose the latter. I filed a complaint with the state insurance division, contacted my agent, reached out to the last adjuster, hired my own painter and withheld final payment to the contractor. I also made it clear that I was prepared to take legal action if necessary. That was not a bluff.
Within a week, things started moving. Seven days later, the insurance company reinspected my home and sent a check covering all but $3,000 of the painting costs. After nearly two years of delays and excuses, progress finally happened when I took matters into my own hands.
Light: What should one look out for?
Kahler: Delay is a common insurer tactic. They’ll repeatedly ask for more documentation, take months to respond or swap adjusters to force you to restart the process—all in hopes that you’ll give up or accept a lower payout.
Another common tactic is the lowball offer. Insurers often rely on software that underestimates damages or send adjusters unfamiliar with actual repair costs. Accepting their first offer without question can be a costly mistake. It’s wise to get independent repair estimates or even hire a public adjuster who works for you rather than the insurance company.
Insurers also deny claims based on fine print, arguing that damage was pre-existing, caused by poor maintenance or excluded under some obscure clause. Knowing your policy inside out and keeping pre-loss photos can help you counter these claims.
Light: What other tricks are there to be aware of?
Kahler: Another one is steering homeowners toward “preferred” contractors who work at discounted rates and may prioritize the insurer’s interests over yours. Getting independent estimates ensures repairs are done properly.
For homeowners stuck in an insurance battle, persistence is key. Withholding final payment until work is complete, filing a complaint with the state insurance division and even considering small claims court can help push a claim forward. If the dispute is within your state’s small claims limit—often between $10,000 and $25,000—filing may push the insurer to settle.
Assuming my contractor would handle everything was my biggest mistake, and it cost me nearly two years of frustration. Even though progress happened quickly once I took control, my claim isn’t over. I suspect I will be filing legal action in small claims court against the insurance company, contractor and insurance agent.
Light: So, what can a policyholder do?
Kahler: If you need to navigate an insurance claim, be persistent and attentive. Keeping records, pushing back on delays and escalating when necessary can mean the difference between being shortchanged and getting the settlement you deserve.
