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Enterprise, OR 97828
They don't teach you this in school
Gain useful tips and insights for car, home, business, farm, contractors, health insurance and more!
Insurance is the safety net we all need but rarely understand fully. As we navigate the complexities of life, it's astonishing how little we're taught about protecting ourselves, our assets, and our future.
That's why we created short blogs to demystify the intricacies of insurance, decode the fine print, and empower you with the knowledge to make informed decisions that could safeguard the life you've worked so hard to build.
Get ready to graduate from the school of insurance wisdom – no cap and gown required!
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Winter Driving Safety: Tips to Avoid Accidents and Insurance Headaches
Winter driving across Oregon, Washington, and Idaho brings unique risks—from icy mountain passes to wildlife collisions. This guide shares practical winter driving tips, what to keep in your car, how insurance applies to winter accidents, and what to do after a crash. Learn how preparation, documentation, and the right coverage can reduce stress and keep you protected all winter long.
Hailie Hillock
Dec 23, 20255 min read
The Insurance Policy Review Checklist: How to Review Your Insurance Coverage & Avoid Costly Gaps
Life changes fast—and your insurance should keep up. This helpful insurance policy review checklist walks you through how to review your coverage, spot common gaps, and ask the right questions so you’re fully protected without paying for coverage you no longer need.
Hailie Hillock
Dec 14, 20255 min read
Auto & Home Insurance Trends to Watch in 2026: What Rural Homeowners & Drivers Should Know
As we head into 2026, Oregon homeowners and drivers—especially in rural areas like Wallowa County—can expect a shift toward slower, more predictable insurance premium changes. While the hard market is finally stabilizing, wildfire risk, supply costs, and insurer restrictions will continue to shape coverage availability. Here’s what these trends mean for you and how to stay protected without overpaying.
Hailie Hillock
Dec 4, 20253 min read
Local Expertise, Personalized Coverage: Why an Independent Agent Is Your Best Ally
In 2017, Hailie Hillock took the leap to continue the Bennetts’ legacy and purchased what is now the Hillock Insurance Agency. Since our team has remained committed to keeping this agency local, independent, and true to its mission of helping our neighbors across Oregon, Idaho and Washington to protect what matters most. We wrote this blog to help you understand what it looks like to work with an independent local insurance agent, and how to decide which path to insurance is
Hailie Hillock
Nov 3, 20254 min read
Prescription Drug Plans: Understanding Your Options and Enrollment
Medicare Part D, Prescription Drug Plans (PDPs), play a vital role in managing your prescription medication costs, but they also come with complexities that require careful consideration. This blog shares the basics of PDPs.
Kathleen Bennett
Oct 2, 20252 min read
How to Change Your Medicare Coverage
There are specific times throughout the year when you can make changes to your Medicare coverages. Shopping your Medicare plan can help save money or get coverages that better suit your current needs.
This guide will help you plan ahead so you can take advantage of opportunities to shop your Medicare coverage.
Kathleen Bennett
Sep 5, 20254 min read
Guide to Medicare Enrollment: When to Enroll and Coverage Options
Confused about Medicare enrollment? Learn when to sign up, when coverage begins, if you should enroll in Part B or Part D, and where you can get assistance enrolling in Medicare. Get clear answers and local guidance.
Kathleen Bennett
Aug 25, 20254 min read
Home Improvement Budgeting in Oregon: 3 Expenses That Surprise Renovators and Remodelers
Learn how to budget for hidden costs like permits, material theft, and contractor changes.
Hailie Hillock
Aug 14, 20253 min read
A Guide to Car Insurance Coverage: How to Choose the Right Options Without Overpaying
Selecting the right car insurance coverage is essential for financial protection and peace of mind. Let’s break down the primary options available to help you make an informed choice.
Hailie Hillock
Jul 13, 20253 min read
Minimum Car Insurance by State: What Drivers in OR, WA & ID Must Know
Understand the insurance requirements to legally drive in Oregon, Washington, and Idaho.
Hailie Hillock
Jul 13, 20253 min read
5 Must-Have Homeowners Insurance Endorsements You Might Be Missing
With the right endorsements, you can customize your policy to better protect your home and avoid costly coverage gaps. Adding endorsements to your policy can help beef it up and prevent you from painful coverage gaps. Let’s explore a few key endorsements many homeowners may find helpful.
Hailie Hillock
May 8, 20255 min read
How Much Will I Pay for Healthcare?: A Guide to Out-of-Pocket Costs
This guide will help you understand out-of-pocket costs including deductibles, coinsurance, and copays so you can plan ahead.
Kathleen Bennett
Apr 8, 20254 min read
Understanding Coinsurance Clauses
Learn what coinsurance is, why it exists, and how you can avoid penalties for being underinsured.
Hailie Hillock
Mar 20, 20254 min read
Understanding Sublimits on Your Insurance Policy
It is important to be aware of limits that apply to high value items. This blog explains sublimits and how to protect your valuables.
Hailie Hillock
Feb 16, 20253 min read
A Private Landlord’s Guide to Property Insurance
Discover essential tips and best practices for landlord insurance in this comprehensive guide.
Hailie Hillock
Jan 18, 20257 min read
How to Get Health Insurance in Oregon
Struggling to find health insurance in Oregon? Discover your options, from Marketplace plans to OHP & CHIP. We’re here to guide you!
Susanna Bonifer
Nov 18, 20244 min read
How Does the Home Claims Process Work?
In this guide, we'll walk through the steps of filing a home insurance claim, what to expect during the process, and tips.
Hailie Hillock
Oct 28, 20243 min read
Medicare Part B: Advantages and When to Enroll
Medicare Part B helps fill in important coverage gaps that can result in unexpected costs. Learn more about this important coverage.
Kathleen Bennett
Mar 21, 20242 min read
Tips for Managing Insurance Costs in Uncertain Times
You may notice a higher than normal increase on your renewals this year. We’ve seen shocking home and auto premium increases across the...
Hailie Hillock
Mar 5, 20244 min read
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