The Most Interesting Tax Location in America (You Guessed It)

In the old Dos Equis commercials, The Most Interesting Man in the World didn’t brag — the world bragged for him.

When it comes to taxes and estate planning, Portland might deserve a similar title.

In my work with estate-planning clients, one topic comes up here more than almost anywhere else:

“Where should we live?”

That question comes up everywhere, of course — but in Portland, it’s different.

Taxes, Geography, and Friction

In most high-tax cities, moving to reduce taxes is a big decision.

If you live in Seattle and want a different tax environment, you’re likely talking about Idaho, Oregon, or California. That’s not just a tax decision — it means leaving behind family, friends, routines, and community. There’s real friction.

The same is true in New York City. NYC taxes are famously high, but New York is also a global hub for finance, media, and culture. For many people, leaving New York means leaving an entire professional ecosystem.

Portland is different.

A Bridge, Not a Goodbye

From Portland, you can cross a river and be in Vancouver, Washington.

Your kids’ schools don’t change much.Your tennis group, hiking trails, restaurants, and friends are still nearby.Your old life is — quite literally — just a bridge away.

From a tax perspective, the difference can be dramatic:

• Oregon has no sales tax

• Washington has no state income tax

For some households, that combination alone meaningfully changes the math — especially as remote work has made geographic flexibility far more realistic than it was even five years ago.

How Unusual Is Portland, Really?

It’s fair to ask whether Portland is truly unique — or just another high-tax city where people complain loudly.

When you look at comparable places, Portland stands out.

New York City, for example, has extremely high state and local taxes. Some people move to New Jersey or Connecticut, but those states still impose income taxes, and the overall tax burden remains substantial. More importantly, New York anchors entire industries. Leaving often means leaving a professional center, not just changing addresses.

San Francisco is another common comparison. California’s income taxes are among the highest in the country, and some residents move to Nevada to escape them. But that move usually involves several hours of distance and a significant lifestyle change. It’s not a subtle shift — it’s a clean break.

Washington, D.C. residents sometimes relocate to Virginia or Maryland. While that can reduce taxes somewhat, neither state eliminates income tax, and the benefit is incremental rather than dramatic.

Chicago residents may look to Indiana, but again, income taxes remain, and the move often comes with meaningful personal and professional disruption.

In each of these cases, reducing taxes generally requires real distance, real disruption, or both.

Portland is different.

Here, a meaningful change in tax exposure can be accomplished by crossing a river — while keeping the same social circle, activities, and lifestyle. Very few metropolitan areas in the country offer that kind of low-friction option.

Why This Matters for Estate Planning

Estate planning isn’t just about documents. It’s about context.

Where you live affects:

• Income taxes during life

• Estate and inheritance taxes at death

• Which state’s laws apply to trusts, probate, and administration

• Long-term planning for retirement and family wealth

In Portland and Multnomah County — often cited among the highest combined state and local tax environments outside of New York City — those questions surface early and often.

And unlike New York, Portland does not anchor a large, immovable industry base. It’s a beautiful, livable city — but many of the higher-paid jobs here are also the kinds of jobs that can be done from somewhere else.

Not a Recommendation — Just a Reality

This isn’t about telling anyone where they should live.

It’s about recognizing that Portland’s geography creates options that don’t exist in many other parts of the country — options that naturally come up in thoughtful estate and financial planning.

Ignoring those options doesn’t make them go away.

Planning Starts With the Right Questions

Good planning starts with questions, not answers.

Where do you want to live — and why?

What tradeoffs matter most to you?

How do taxes, family, lifestyle, and legacy intersect?

In Portland, those questions are especially interesting.