A once-per-year checkup where you do two things:

The goal is not to chase the cheapest policy. The goal is best value—reasonable premium for the right protection.

Insurers update rates based on many factors (location, claims trends, repair costs, inflation, catastrophic weather risk, vehicle repair costs, etc.). A homeowners insurer like Travelers explains that severe weather and rising repair/material costs contribute to higher home insurance rates. 

That means your premium can rise even if you’ve done nothing “wrong.” Reviewing yearly gives you a chance to:

Auto rates can change with:

Many consumer insurance guides recommend shopping after a major life change (moving, retirement, mileage drop) or before renewal. 

55+ angle that saves money: If you drive fewer miles now, ask about low-mileage or usage-based discounts.

Home insurance is one of the fastest “creeping” costs, and it’s also the most dangerous to ignore because underinsurance can be devastating. Rate increases are commonly linked to repair/rebuild cost inflation and weather-related losses. 

What to check yearly:

The Insurance Information Institute recommends comparing quotes and verifying how discounts apply (especially bundling). 

Medicare coverage is not “set it and forget it.”

CMS confirms the Medicare Open Enrollment Period (often called Annual Enrollment) runs October 15 to December 7 each year, when people can change Medicare health and drug plans for the following year. 

If you’re in Medicare Advantage, Medicare.gov explains you also have a Medicare Advantage Open Enrollment Period January 1–March 31 (only for people already enrolled in Medicare Advantage), to switch plans or return to Original Medicare and join Part D. 

Why this belongs in “re-quote season”:

Plans change costs, drug formularies, provider networks, and pharmacy networks. CMS specifically notes plans can make changes each year in cost, coverage, and networks—making annual review important. 

A life insurance review isn’t about “dropping it.” It’s about matching coverage to your current life:

This is a sensitive category, so the best approach is: review purpose first, then consider changes with a licensed professional.

Pick one month you’ll repeat every year. Two good options:

This is the most practical because you’re already near a decision point and can switch if needed.

Some industry sources suggest December can be a good time to shop because some insurers adjust rates into the new year, but the biggest driver remains “life events” and renewal timing. 

Choose your renewal month (or the month before) and make it your annual insurance checkup.

For each policy, grab the declarations (“dec”) page:

Use these for auto + home/renters + supplemental:

Use a consistent “apples-to-apples” approach. The NAIC’s auto insurance shopping tool emphasizes comparing similar coverage and noting deductibles when you shop. 

Rule: Never compare prices unless coverage and deductibles match.

Bundling can create discounts; NAIC notes bundling is a common strategy where insurers offer discounts for buying multiple policy types from the same company. 

But the Insurance Information Institute warns bundling doesn’t always guarantee the cheapest overall combination and recommends comparing bundled vs separate quotes. 

Before switching:

Avoid any gap in coverage.

“Hi, I’m reviewing my budget and doing my annual policy checkup. Can you re-quote my policy and check for any new discounts I qualify for? I’d also like to compare deductible options and confirm my coverage is still appropriate.”

“If I bundle my auto and home/renters with you, what is the total combined cost? And can you show me the premium difference bundled vs separate?”

(Then verify the discount appears on the declarations page.) 

“I’m reviewing my coverage during Medicare Open Enrollment. I want to confirm my doctors and prescriptions are still covered and compare total yearly costs.”

CMS notes plans can change costs and networks annually, so reviewing during Oct 15–Dec 7 matters. 

Cheaper can mean higher deductible, less coverage, or narrower networks.

Fix: Compare total protection, not just price.

Bundling can help, but compare both ways. 

Repair and rebuild costs rise. If coverage hasn’t kept up, you may be underinsured. 

CMS explicitly notes plans can change cost, coverage, and networks annually. 

Insurance is one of those expenses that can creep up quietly—especially homeowners and auto. An annual Insurance Re-Quote Season helps you stay in control:

Even one good re-quote can save meaningful money over a year—without sacrificing coverage.

With care,

Mike Bridges

Founder, The O55 Report