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The ARS Associates Insurance Blog — Answers to Real Questions

Why I Write About Insurance

Medicare rules change every year. Oregon has its own rules on top of the federal ones. Annuities are widely misunderstood. Health sharing plans are growing in popularity and barely covered accurately online.


I write this blog because the questions my clients ask are the same questions thousands of clients are searching for right now — and general national advice doesn't always apply here. The Oregon Birthday Rule, local plan availability, annual enrollment windows, and Part D changes all deserve clear, current, location-specific answers.


When you find something useful here, there's a free consultation waiting if you want to take the next step.

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Common Questions About This Blog and Working With Chris

  • Is this blog written by Chris Schaefer directly?

    Yes. Every post reflects my experience working with real clients across Oregon and 15 other states. When Medicare rules change or a question keeps coming up in consultations, that's what I write about.

  • When can I switch Medicare plans in Oregon?

    The main window is the Annual Enrollment Period, which runs October 15 through December 7 each year. There are also Special Enrollment Periods triggered by qualifying life events. Oregon residents with Medicare Supplement plans also have additional protections under the Oregon Birthday Rule — I cover this in detail in a dedicated post.

  • What is the Oregon Birthday Rule?

    Oregon law gives Medigap policyholders a 30-day window each year around their birthday to switch to a plan with equal or lesser benefits — without underwriting. It's one of the strongest consumer protections in the country for Medicare Supplement holders, and most people outside Oregon don't have access to it.

  • Should I get Medicare Advantage or Medicare Supplement?

    It depends on your health, your finances, your doctors, and how much uncertainty you're comfortable with. There's no universal right answer, which is why I wrote a full comparison and why I offer free consultations to work through it with you directly.

  • Can I get personalized advice here, or is this just general information?

    The blog is general education — it's not a substitute for a conversation about your specific situation. If something you read raises a question or feels relevant to your coverage, schedule a free consultation and we'll apply it directly to your circumstances.

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