The “Inner Cleveland” of Trendy Cities


Check out these photos and try to guess where they were taken. If you thought Cleveland, Pittsburgh, Detroit, Buffalo, Cincinnati, or a dozen other Rustbelt towns you’d be mistaken, although your confusion is completely understandable. It’s actually Portland, Oregon – that bastion of liberal, crunchy, hippie, yuppie, hipster, eco-friendliness. Go figure. I’m not putting down Portland. Portland is great. I love Portland. I’m making a point about the reputation of some cities and how we perceive places differently based on a lot of vague stereotypes. If the only images we ever saw of Portland all looked like this it would be hard to persuade people to migrate there – even if the photos don’t portray the complete reality on the ground.

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To be perfectly honest, Portland is a small blue collar city out in the sticks with a fairly recent trendy overlay. Its economy is fair-to-middling. Stable, but nothing to write home about. It’s primary source of dynamism comes from inflows of cash, talent, and people from other more expensive west coast cities who seek out a higher quality of life at a lower price point. That migration is fueled by the popular image many people have about the city more than the reality on the ground. Over time this branding becomes a self-fulfilling prophecy. Now check out these next photos.

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When you look at these pictures what do you think of? Portland? Seattle? Boston? Chicago? It’s actually Cincinnati.

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How about these photos? San Francisco? Maybe a cool part of LA? Nope. It’s Pittsburgh.

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How about these photos? Brooklyn? Chicago? Boston? How about Buffalo? Yep. Buffalo.

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Are you looking for a great walkable vibrant neighborhood, but really want a single family home with a patch of garden to go along with all the cool nearby shops and fun stuff on Main Street? Maybe something with a bit of historic charm instead of a cookie cutter tract home? Well, for north of $500,000 you can get one of these great places in Portland. Or…

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For about $200,000 you could get something like this in Buffalo. Don’t have $200,000? If you’re willing to work on a fixer upper in a transitional neighborhood really close to the areas that have already gentrified you can find something for $50,000.

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How about one of these in Cincinnati for between $50,000 and $200,000?

Will you make as much money in Cincinnati, Pittsburgh, or Buffalo as you might in Seattle, Chicago, or Brooklyn? No. But when your housing cost has been radically reduced you really don’t need nearly as much cash. It isn’t how much you earn that matters. It’s how much you have left over at the end of the month that determines how well you live. Personally I spend 90% of my life within a five block radius of my apartment in San Francisco. Do I love having ready access to the rest of an amazing city? Absolutely. Could I afford to enjoy most of what San Francisco has to offer if we hadn’t bought our place a million years ago when the Mission was still a cheap funky neighborhood? Not even close.

Here’s my advice to both young people who are just starting out as well as older people who are struggling to manage in a tough economic environment. Stop fighting expensive housing markets. Stop trying to wedge yourself into an overpriced shoe box apartment in a mediocre neighborhood in a top tier city. Stop driving an hour and a half out to an isolated subdivision just to hold on to your status in a big metroplex. It’s not worth it. The interior of the country is absolutely full of amazing places at a price you can comfortably afford. Give yourself and your family a big raise and leave the coast behind.

John Sanphillippo lives in San Francisco and blogs about urbanism, adaptation, and resilience at He's a member of the Congress for New Urbanism, films videos for, and is a regular contributor to He earns his living by buying, renovating, and renting undervalued properties in places that have good long term prospects. He is a graduate of Rutgers University.

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I think that this is very

I think that this is very trendy city, as we can see on this marvelous pictures here.

Incompatable Argument

With so many 1/2 truths and incompatible arguments in this piece, I'm not sure where to begin. At one side of the country in the Midwest, we have a conservative haven, along with all the regressive policies that go with the GOP. The result? College students leaving in droves for the coasts, and select liberal areas in the south. The other? Extensively funded transit systems, rich art scenes, and expansive economies that offer an array of opportunities for college graduates. Are these things not worth paying more for? As much as they are bashed for being narcissistic self seeking kids, today's college graduates have done their research, and well before graduation have concluded that their degrees will be valued more in liberal strong holds. This is something that will never change, and no matter how you paint a 50,000 house in Cleveland, there is still the underlying reason why that house is only 50K.

Yes and no

Half truth? Sure. I agree that there are different perspectives to explore here.

I fled southern suburban New Jersey as a teenager and never looked back. It was dull, close-minded, there was no culture, nothing but low paying service jobs, AND I got pulled over by the police whenever I rode my bike because it constituted "probable cause" in a neighborhood full of uptight insecure white people. I escaped to San Francisco and I'm very happy I did so. I was lucky to arrive at a time when it was still possible for mere mortals to buy a modest little place at a tolerably expensive price. That's one half of the truth.

The other half is that I've lived here long enough to see several waves of new young people arrive, burn out after a few years, and then leave. I've also seen many older folks cash out and take their money elsewhere. They aren't going from San Francisco to Brooklyn. They're working their way down the food chain and reinventing the second and third tier cities that have largely been abandoned by conservatives and are ripe for reinvention along different lines. There's a big gap between Mississippi and the Great Lakes with all sorts of places in between. Ever been to Yellow Springs, Ohio? It's magical and wonderfully liberal if you like that sort of thing.

Yes and no

I've actively been looking at real estate in the Rust Belt for the last couple of years. I could sell my one bedroom apartment in San Francisco for $875K (paid almost nothing for it when the Mission was a cheap undesirable neighborhood years ago) and pay cash for an entire building or two in a great neighborhood near the university and downtown in Cincinnati, Pittsburgh, etc. In middle age I'd have no debt, steady rental income, access to culture, and an airport to escape the snow in January and heat in August. That's a pretty fabulous retirement plan. Better than a 401K that could implode at any moment and a crappy condo in Orlando with a view of the Interstate.

An alternative might be to hold on to the San Francisco apartment and diversify by buying something affordable elsewhere as a Plan B.

you don't need to go to the rust belt

You don't need to go to the rust belt if you want much less expensive housing. There's also Stockton or Fresno. Have you considered Hilo?

No to Stockton and Fresno, yes to Hilo

Funnny you should say Stockton, Fresno, and Hilo... As a younger man in the 1990's I did in fact looked at the first two and ruled them out because I didn't like the local culture (way too conservative for a gay boy) and the weather was far too hot and dry. (Some people hate winter, but I can't stand 110 degrees at midnight.) But Hilo... I did go to Hilo and did in fact buy property there which I still own.


Doubtful the author would leave the temperate West for Cleveland or Indianapolis even if he didn't own his own place in the Mission.