Questions From the Front Lines of the Housing Crisis

I recently spent time in Des Moines, Iowa, with planners, local officials, housing advocates, and development professionals talking about one of the most difficult questions facing American cities today: How do we make housing more affordable without destroying the places people already love?

What struck me most was not the disagreement. It was the seriousness of the questions.

People are wrestling with real tensions: how to add housing without losing neighborhood character, how to create walkable places in communities built around cars, how to help elected officials understand long-term financial consequences, and how to support small-scale development in a system designed for large institutional players.

What follows is an edited version of that conversation, not a transcript, but a summary of the themes and questions people raised, along with my responses.

Q: If building more housing is supposed to solve affordability, why does it still feel impossible for ordinary people to find homes they can afford?

There’s a theory that dominates a lot of housing conversations right now: If we simply build enough housing — especially market-rate housing — prices will eventually come down through a process economists call filtering.

There’s some truth to this idea. But I think it misses the core problem.

The issue is not simply that America lacks housing units in the aggregate. In fact, nationally, we actually have more housing units per person today than we did before the 2008 housing crash. The issue is that we don’t have the right kinds of housing.

We have lots of large homes designed for mid-20th century family patterns. Meanwhile, we increasingly have one-person and two-person households. We have seniors living alone in houses that are too large and too expensive to maintain. We have young people who don’t need — and can’t afford — four-bedroom homes with large yards.

The housing market keeps producing what is easiest to finance and regulate: large single-family homes.

But the missing product in most communities is smaller, flexible, modest housing: duplexes, backyard cottages, starter homes, small apartments, and conversions within existing neighborhoods.

That’s why Strong Towns focuses so heavily on what we call “Housing-Ready” reforms: legalizing small-scale, incremental housing that can fit naturally into neighborhoods.

The challenge isn’t simply quantity. It’s mismatch.

Q: How do you convince communities to accept more housing when residents are deeply attached to neighborhood character?

I actually think this is the wrong framing.

Too often, we talk as if neighborhoods have only two options: remain frozen exactly as they are today, or become unrecognizable. But healthy neighborhoods have always evolved.

I often explain this by talking about my daughter. I can look at photos of her as a baby, as a toddler, as a teenager, and now as an adult. At every stage, she was unmistakably the same person. The character remained. But she matured.

Neighborhoods should work the same way. A healthy neighborhood is not static. It changes gradually over time. The question isn’t whether change happens. The question is whether the change feels like a natural evolution of the place.

That’s why the most successful housing reforms are usually modest and incremental. A duplex tucked into an existing block. A backyard cottage behind a home. A starter home on a smaller lot. These things don’t erase neighborhood character. They allow the neighborhood to mature.

When people resist housing, they are often reacting to the fear that change will be imposed in a way that feels disconnected from the place they love.

The answer is not to eliminate change. It’s to make the next increment of growth feel compatible with what already exists.

Q: What do you say to fast-growing suburbs that believe they’ve “figured it out” because growth is booming?

Many rapidly growing suburbs are living through what I call the illusion-of-wealth phase of the Growth Ponzi Scheme.

They just received a new interchange. Development is booming. Retail is expanding. Tax revenue is increasing. Everything feels successful. And because things feel successful, it becomes emotionally difficult to ask hard questions about long-term liabilities.

Growth creates a sugar high.

When communities are experiencing rapid growth, there’s a natural tendency to assume the growth itself proves the model is working. Officials start believing their success is the result of superior planning or better management rather than recognizing that they may simply be at the beginning of a long financial cycle.

That makes it hard to have conversations about long-term maintenance obligations, infrastructure replacement costs, or financial fragility.

The challenge is that suburban infrastructure systems are incredibly expensive over time. Roads, pipes, and utilities eventually need replacement. If the tax base created by that growth isn’t productive enough to cover those obligations, the apparent prosperity eventually becomes a financial burden.

The places that are hardest to reach are often the places currently experiencing the strongest growth. Not because people are hostile, but because they don’t yet feel the consequences.

Q: Small towns and outer-ring suburbs want more housing diversity, but residents worry about parking, traffic, and losing the feel of the community. Is there a realistic path forward?

This is one of the hardest challenges in America right now.

Many small towns near major metro areas are trapped between two identities. Historically, they functioned as real towns: compact, productive, walkable places with local businesses and strong social cohesion. Today, many have become auto-dependent bedroom communities layered on top of small-town infrastructure.

That combination is financially and culturally difficult.

The tension residents feel around parking and cars is real. If everyone depends on driving for every trip, adding more housing naturally increases stress on the system.

But the solution isn’t to stop evolving. The solution is to create alternatives to constant car dependence.

The more people can walk or bike for short trips, the less pressure there is on parking and traffic. Even modest improvements matter. Sidewalks. Connected street networks. Local businesses near homes. Reliable regional transit links.

The goal is not to eliminate cars overnight. The goal is to gradually create a community where households can rely a little less on multiple vehicles.

That transition is difficult. But the alternative is often continued financial fragility and declining viability.

Q: Why is it so hard to get elected officials to support incremental housing reforms?

Because local governments rarely frame development decisions around financial outcomes.

Most council conversations focus on abstract concepts: growth, housing demand, neighborhood concerns, environmental impacts, traffic. What’s often missing is the long-term fiscal analysis.

One city in Texas has started doing something incredibly important. For every development proposal, staff presents a straightforward financial analysis:

• What infrastructure costs will this create?
• What long-term maintenance obligations come with it?
• What tax revenue will it generate?
• Does the math work over time?

Asking and answering those questions -- which are reasonable questions that nearly everyone has -- changes the conversation.

When elected officials can clearly see whether a project strengthens or weakens the city financially, they start asking better questions. This doesn’t mean cities stop growing. It means cities become more disciplined about what kinds of growth they support.

The role of professional staff is not to make decisions for elected officials. The role is to help them fully understand the consequences of the decisions they are making.

Right now, most communities are making major financial commitments without seeing the complete balance sheet.

Q: If cities want smaller, more affordable housing, why don’t developers build it?

Because the current financial system strongly favors large-scale, standardized development.

Single-family subdivisions and large apartment projects fit neatly into the financing system. Banks understand them. Appraisers understand them. Secondary mortgage markets understand them.

Small-scale incremental projects — duplex conversions, small mixed-use buildings, backyard cottages — often don’t fit conventional financing products.

This is one of the central themes in Escaping the Housing Trap. We’ve built an incredibly efficient financial system for producing one very narrow type of housing product. And we’ve largely eliminated the financing ecosystem that once supported incremental development.

That’s why many of the developers capable of building the housing we actually need are not large institutional firms. They’re local entrepreneurs.They’re people with more passion than capital.

Often, they’re willing to take on projects because they care about the neighborhood, the building, or the outcome, not simply because the spreadsheet says it maximizes returns.

Cities that want more incremental housing need to actively support these local developers. That means simplifying processes, reducing uncertainty, offering preapproved plans, and helping create financing relationships that make small projects viable.

Q: Is tax increment financing (TIF) ever appropriate for housing?

Usually, I’m deeply skeptical of tax subsidies for development.

Most TIF programs end up subsidizing projects that either don’t strengthen the city financially or would have happened anyway. But there are exceptions.

I talked about one city that created a very targeted housing program focused specifically on small starter homes in neighborhoods with long-term disinvestment.

The key difference was precision.

They weren’t simply subsidizing “growth.” They identified a very specific housing gap and used a targeted tool to fill it. That’s fundamentally different from using public subsidies to support speculative large-scale development.

The lesson is not that every city should embrace TIF. The lesson is that cities should be extremely clear about the problem they are trying to solve and honest about the long-term financial implications of the tools they use.

Q: What gives you hope?

Honestly, these questions.

What I experienced in Des Moines was not a room full of people pretending they had easy answers. It was a room full of people wrestling honestly with hard realities. That matters.

American cities are facing enormous structural challenges. Our housing system, transportation system, and development patterns are all deeply interconnected. There are no quick fixes.

But there are people all over the country trying to move their communities in healthier directions. Incrementally, patiently, and thoughtfully. That’s how places become stronger.

Not through grand plans. Through thousands of small acts of adaptation, stewardship, and reform carried out by people who care deeply about where they live.