On the Road to Home

Michael Flack

WHEN MOST PEOPLE retire, they have a good idea where they’ll live. It might be where they currently reside, or where they vacation, or a place near their children or grandchildren. Whatever the case, there’s usually a limited number of possibilities.

But what if you move to a new city for the last two years of your working life, never vacation in the same place twice, don’t own a vacation home, are childless and—upon retirement—sell your home, sell most of your stuff, pack the rest in a POD and then travel the world for the next year?

In that scenario, which just happens to be one that my wife and I found ourselves in, the world is a blank canvas and identifying a new home becomes just a little more complicated.

One option could have been to review articles such as Kiplinger’s “The Best Places to Retire in the World,” and then plan accordingly. Or maybe a spreadsheet could be created that compares different locations. But instead, Susan and I decided to take a less analytical and more Kerouacian approach. We would hit the road, man, and personally interview cities until one made the scene. Can you dig it?

We, of course, were looking for that perfect candidate—you know, the one with low taxes, modest housing costs, reasonable cost of living, great culture, James Beard award-winning restaurants, outstanding health care and an airport with direct flights to Paris, Tokyo and Hawaii.

I was immediately attracted to cities in Alaska, Florida, Nevada, South Dakota, Texas, Washington and Wyoming for the obvious reason: taxes. All but Washington were summarily dismissed due to the increased possibility of heat stroke, frost bite or cabin fever. Even Washington was eventually overlooked, because we never made it that far west.

After touring cities like Ann Arbor and Boulder, I realized that the successful candidate needed a certain amount of grit. Not too much, as there is a fine line between “urban lifestyle” and some half-naked guy screaming obscenities in the middle of the street. I wanted a dynamic interaction of races and cultures, access to decent pizza and some city noise. Not necessarily the sound of gun shots, but maybe a siren every now and again.

In our search for grit, Detroit was interviewed. The city had fallen on hard times and therefore I thought it might make for a strong candidate. It had a decent tax structure, though with much more sprawl than I imagined. The downtown had bottomed out a few years earlier, and was now filled with activity and a significant number of cranes.

In fact, the area was becoming quite fashionable. As it turns out, maybe too fashionable, as real estate prices were soaring. I also happened to interview Pulitzer-prize-winning, man-on-the-street journalist Charlie LeDuff, who informed me that much of the “new” Detroit was a facade, built on debt and endemic corruption.

Denver looked quite promising, with a good tax structure, some grit and no humidity. Unfortunately, the word was out, and property values reflected it, plus it was too late in life to learn to ski or develop a daily skin-care regimen.

Pittsburgh, another city the Flacks didn’t choose

Pittsburgh also looked promising, with affordable real estate, cultural offerings and a fair amount of grit. It’s actually quite picturesque and ranked as the second most “livable city in the U.S.” by The Economist. We visited in the fall and the weather was decent, though locals informed us the winter can be a little “chilly,” with more than a little “precipitation.” And, oh yeah, air quality could be an issue. Still, it was shortlisted.

It was starting to get a little cold, so I figured a little southern sojourn was in order. Savannah was purely an informational interview. I knew going in that it wouldn’t make the cut. Yes, it’s easy to fall in love with the place: the food, the hospitality, the city squares and the laid back way of life. I even found myself looking at real estate. But then a few days of warm, humid weather set me straight, reminding me of my two years in Houston: the four months of fall never made up for the eight months of summer.

After a stopover in Texas to vote, we decided to hunker down in Kansas City to ride out the pandemic. While the tax structure in the Paris of the Plains wasn’t optimal, housing costs were quite reasonable, it had good health care and everybody was really, really nice.

Kansas City, where the wandering Flacks finally settled

We ended up falling in love with the neighborhood where we were staying. It had a small town feel, but was located a five-minute walk from a downtown area, and it offered the perfect amount of grit. Unfortunately, none of the houses we looked at was worthy.

But then, just as the interview was drawing to a close, we came across a modern townhouse condo filled with light, a dramatic three-story staircase and an owner who was in a hurry to sell. In the end, the specific house and neighborhood were the deciding factors. Also, it may have been that the road was getting just a little old and we were hankering to put down some roots.

Looking for the perfect retirement location is much like investing in the stock market. All the information is very public, with a never-ending discussion in The Wall Street Journal, Kiplinger and a sizable portion of the internet. Result? Finding that income-tax-free beach community, offering low property taxes, low home values and low cost of living, plus a symphony hall and the Mayo Clinic nearby, is much like finding that wide moat, high-yield, increasing dividend, tax-advantaged security that’s selling at a 13% discount.

You may wonder about the one criterion I didn’t mention during the interview process: politics. When I once mentioned the desire to live in San Francisco, a friend dismissed it as “too liberal.” I agree. But I’d live there in a New York minute if it weren’t for the ridiculous cost of living. Before some of you say “exactly,” one thing I learned during the interview process: Almost every city of any size leans just a little to that side of the political spectrum. If you want urban, it comes with the territory.

Michael Flack blogs at He’s a former naval officer and 20-year veteran of the oil and gas industry. Now retired, Mike enjoys traveling, blogging and spreadsheets. Check out his earlier articles.

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