July 23, 2026
Auto Insurance Rate Hike Denver 2026
I got my auto insurance renewal last month and I actually called my agent to confirm it was correct. $2,180 for six months. That is $363 a month. For ...
Blog
Real stories, real numbers, no fluff. Written by a former senior underwriter.
July 06, 2026
Chicago Heat Dome Insurance Denial
Why My Home Insurance Claim Got Denied After the Chicago Heat Dome—And What I Did About It Marcus Whitfield The adjuster looked at my basement and sai...
July 06, 2026
Dropped Collision Saved 900 Regretted It
The deer came out of nowhere. One second I was driving home from a late shift at the hospital, cruising down I-70 at 65 mph, singing along to a song I...
June 27, 2026
The Renters Insurance Claim That Taught Me Everything
The Renter's Insurance Claim That Taught Me Everything About Coverage Gaps I was on the Kennedy Expressway when my phone rang. It was a Tuesday in Mar...
June 24, 2026
The Widow Two Kids And A Policy That Paid Nothing
The Widow, Two Kids, and a Policy That Paid Nothing I was reviewing files in my home office when my phone rang. It was a Tuesday afternoon, the kind o...
June 10, 2026
What the Claims Adjuster Didn't Tell Me After My Car Accident | CoverageCheckr
What the Claims Adjuster Didn't Tell Me After My Car Accident I learned this lesson on a rainy Tuesday night on the Kennedy Expressway. I was drivin....
June 09, 2026
The Year I Almost Became a Statistic (And Why I Left Underwriting) | CoverageCheckr
The Year I Almost Became a Statistic (And Why I Left Underwriting) You’d think someone who priced life insurance for a...
June 08, 2026
The Self-Employed Guitar Teacher Who Didn't Think He Needed Disability | CoverageCheckr
The Self-Employed Guitar Teacher Who Didn't Think He Needed Disability I hear that at least once a month. Usually from a self-employed person – a con...
June 07, 2026
The Reinsurance Market Is Tightening: Your Home Insurance Premium Will Reflect It | CoverageCheckr
The Reinsurance Market Is Tightening: Your Home Insurance Premium Will Reflect It I was on a call last month with a former colleague who still w...
June 06, 2026
The 10-Minute Disability Insurance Checkup for Freelancers and 9-to-5ers | CoverageCheckr
The 10-Minute Disability Insurance Checkup for Freelancers and 9-to-5ers That’s the question I start every disability checkup with. Most people sta.....
June 05, 2026
The $50,000 Surgery That Cost Me $200 Thanks to a PPO | CoverageCheckr
The $50,000 Surgery That Cost Me $200 Thanks to a PPO I still have that statement in a file folder. Not because I’m proud of the number – though I...
June 04, 2026
Replacement Cost vs. Market Value: The $100,000 Home Insurance Mistake | CoverageCheckr
Replacement Cost vs. Market Value: The $100,000 Home Insurance Mistake I ask this question at every home insurance revie...
June 03, 2026
NAIC AI Transparency Law: What It Means for Your Auto Insurance Rate | CoverageCheckr
NAIC AI Transparency Law: What It Means for Your Auto Insurance Rate I was at a cookout last summer. My neighbor...
June 02, 2026
Medicare Advantage Network Restrictions: What Illinois Seniors Need to Know | CoverageCheckr
Medicare Advantage Network Restrictions: What Illinois Seniors Need to Know I got a cal...
June 01, 2026
Life Insurance Needs Estimator: Why One Times Salary Is a Lie | CoverageCheckr
Life Insurance Needs Estimator: Why One Times Salary Is a Lie I see this every wee...
May 31, 2026
Insurance Deserts: Why Your Zip Code Matters More Than Your Driving Record | CoverageCheckr
Insurance Deserts: Why Your Zip Code Matters More Than Your Driving Record...
May 30, 2026
Illinois Homeowners Insurance Rates Are Up 22% in 2026: Here's Why | CoverageCheckr
Illinois Homeowners Insurance Rates Are Up 22% in 2026: Here's Why I opened that renewal notice on a Tuesday morning, coff...
May 29, 2026
How to Use the Auto Coverage Optimizer to Stop Overpaying | CoverageCheckr
How to Use the Auto Coverage Optimizer to Stop Overpaying I’ve run this for hundreds of people. And nine times out of ten, they’re p...
May 28, 2026
How to Read a Health Insurance Summary of Benefits Without Losing Your Mind | CoverageCheckr
How to Read a Health Insurance Summary of Benefits Without Losing Your Mind That’s not false modesty. A few years ago, I was helping my...
May 27, 2026
How to Optimize Your Auto Coverage Based on Your Car's Actual Value | CoverageCheckr
How to Optimize Your Auto Coverage Based on Your Car's Actual Value I say this at least three times a week. Someone calls me, angry about thei...
May 26, 2026
How to Find Your Insurance Coverage Gaps in 20 Minutes | CoverageCheckr
How to Find Your Insurance Coverage Gaps in 20 Minutes I don’t blame you. I used to write those policies for a living, and even I don’t rea...
May 25, 2026
How to Appeal a Homeowners Insurance Claim Denial: Step by Step | CoverageCheckr
How to Appeal a Homeowners Insurance Claim Denial: Step by Step I learned that number from a claims adjuster I used...
May 24, 2026
How We Almost Lost Our House to a Flood That Wasn't Covered | CoverageCheckr
How We Almost Lost Our House to a Flood That Wasn't Covered I remember exactly where I was standing. Kitchen. Wednesday evening. A pan of...
May 23, 2026
Health Plan Comparator: How to Compare Three Plans Side by Side | CoverageCheckr
Health Plan Comparator: How to Compare Three Plans Side by Side Open enrollment starts next week. You have three options. How do you choose? I get t....
May 22, 2026
Employer Health Plan vs. Marketplace: Which One Saves You More? | CoverageCheckr
#26 Employer Health Plan vs. Marketplace: Which One Saves You More? “Your employer says they cover 80% of premiums. But are you actually saving money?...
May 21, 2026
Embedded Insurance: The $5/Month Protection You Don't Need | CoverageCheckr
#25 Embedded Insurance: The $5/month ‘Protection’ You Don’t Need “Add phone protection for only $7.99? No thanks.” I clicked “no” so fast my finger a...
May 20, 2026
Disability Coverage: Are You One Injury Away From Financial Ruin? | CoverageCheckr
Disability Coverage: Are You One Injury Away From Financial Ruin? I ask this question at every financial checkup. Most peop...
May 19, 2026
Cyber Insurance for Families: Do You Really Need It? | CoverageCheckr
Cyber Insurance for Families: Do You Really Need It? I was on a panel last year about emerging insurance risks. Someone from the...
May 18, 2026
Climate Risk Modeling and Your Home Insurance: The New Reality | CoverageCheckr
Climate Risk Modeling and Your Home Insurance: The New Reality I got an email from a client in Des Plaines – let’s call her Mrs. Chen. She’d lived in...
May 17, 2026
Chicago Flood Zone Remapping: How to Know If You're at Risk | CoverageCheckr
Chicago Flood Zone Remapping: How to Know If You're at Risk I found out because my neighbor got a l...
May 16, 2026
AI Underwriting Algorithms: Why You Might Be Paying More for No Reason | CoverageCheckr
AI Underwriting Algorithms: Why You Might Be Paying More for No Reason I hear this question at least once a week. Someone pulls into my virtual offic...
May 15, 2026
A Widow, Two Kids, and a Policy That Paid Nothing | CoverageCheckr
A Widow, Two Kids, and a Policy That Paid Nothing I was reviewing files in my home office when my phone rang....