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How to Compare Insurance Policies: Tips for Getting the Right Coverage


Compare insurance policies, dude, I’m still recovering from the week I tried to do it while my kitchen looked like a tornado hit a Wawa. Rain was just slamming my fire escape in Hoboken—felt like the sky was personally mad at me—and my AC unit was wheezing worse than my uncle after Thanksgiving. I had three auto quotes, a half-eaten cheesesteak going cold, and zero chill. Like, who even compares insurance policies at 1 a.m. with grease on their fingers? Me. That’s who.

Why I Had to Compare Insurance Policies (Thanks, Basement Flood)

So yeah, September nor’easter. Basement turned into a kiddy pool. My old yearbooks? Floating. My dignity? Drowned. Turns out my homeowner’s policy had this bullshit clause about “gradual seepage” that nobody ever mentioned. I was mopping with one hand, googling “compare insurance policies” with the other, while my cat gave me the side-eye from the stairs like, “You had one job, human.”

My First Dumb Move in Insurance Policy Comparison

Jumped on the first comparison site I saw. Filled out everything—my dented 2012 Civic, that one Philly ticket I swear was a setup. Got three quotes. Felt smart for like five seconds. Then I actually read the policies and saw Company A excluded “acts of raccoons” (I wish I was kidding) and Company B wanted $200 extra for the same coverage. My highlighter died around page 47. RIP.

Rainy diner window, scuffed sneakers below neon.
Rainy diner window, scuffed sneakers below neon.

How to Compare Insurance Policies Without Wanting to Yeet Your Laptop

Here’s what I wish I knew before I spiraled:

  • Don’t just chase the lowest price — almost went with a $42/month quote until I saw the deductible was $2,500. Bro, I don’t have that in my mattress.
  • Declarations page is your best friend — it’s the cheat sheet. I printed mine and color-coded: green for coverage, red for exclusions, yellow for “what the hell does this mean?”
  • Bundling sounds cool but read the fine print — saved $180 bundling auto + home but lost roadside assistance. Had to add it back. Annoying.

The Tools That Stopped My Insurance Policy Comparison Meltdown

Found this independent site where you can slide coverage up and down in real time. No, they didn’t pay me—wish they did, I’d upgrade from Folgers. Also, my state’s insurance dept has a free worksheet that made me feel like a grown-up for once.

The “Oh Sh*t” Moment Comparing Insurance Policies

I was so focused on car insurance I forgot my renter’s add-ons. My laptop? Not covered for “mysterious disappearance.” I’ve lost three chargers this year. Added that rider for $27 and felt like I hacked the system.

Coffee-stained policies with "WHY SO MANY EXCLUSIONS???"
Coffee-stained policies with “WHY SO MANY EXCLUSIONS???”

Talking to Actual Humans (Weirdly Helpful)

Called agents. First one sounded like a robot reading legalese. Second one—Sarah from some local company—laughed when I asked about raccoon damage and actually explained sh*t. “What if a deer in a reflective vest hits my car?” She didn’t even flinch.

When Comparing Insurance Policies Gets Straight-Up Bizarre

Ended up with a policy that covers “falling objects” because my neighbor’s drone took out my grill last 4th of July. Also learned some policies cover “civil commotion”—very 2025 vibes. Anyway, my new premium is $42 less a month and actually covers my stuff.

My Final (Sleep-Deprived) Tips for Insurance Policy Comparison

  1. Screenshot every quote—my phone now has a folder called “Insurance Hell 2025”
  2. Set a 45-minute timer or you’ll go insane
  3. See an exclusion that makes you go “wait, huh?”—call immediately

Comparing insurance policies ain’t glamorous. It’s me in crusty sweats, cold fries, deciphering tiny font while my cat judges me. But now a flood wouldn’t bankrupt me, my laptop’s covered if it vanishes into the void, and I saved enough for real coffee.

Your turn—what’s the dumbest exclusion you’ve seen while comparing insurance policies? Spill in the comments. And don’t wait for a flood like I did. Start comparing here—tell ‘em the raccoon guy sent ya.

(wait, did I spell “exclusions” wrong up there? whatever, you get it)