Damned if You Do, Damned if You Don’t

By: J. David Chapman, PhD, / May 8, 2026

In the rental property business, we spend a lot of time thinking about what is fair. Fair rent. Fair treatment. Fair expectations. For years, many landlords, including Julie and me, have approached lease renewals with a simple philosophy: if you have a good tenant, take care of them. Keep rent increases modest. Sometimes don’t raise the rent at all. The thinking is straightforward. It creates stability for the tenant and predictability for the landlord.

Everyone wins. Or so we thought. In my book Landlord! Balancing Proft, Property, & People scheduled for a summer 2026 release, I highlight what economists call an “affordability trap.”  In many markets, tenants are remaining in place not because they want to, but because they cannot afford to leave. Giving up a below-market lease often means stepping into a significantly higher rent, sometimes hundreds or even thousands more per month.

So, they stay. At first glance, that sounds like the very outcome landlords are trying to achieve. Long-term tenants reduce turnover, limit vacancy, and create consistent income. In the language of property management, they are ideal.

But this is where the dilemma begins. If tenants are staying primarily because they are financially stuck, then the stability we are proud of may not be the kind of stability we think it is.

It may be stagnation. And that creates a “damned if you do, damned if you don’t” situation for landlords. If you aggressively raise rents to market levels, you risk displacing tenants and contributing to the very affordability challenges we all recognize. If you hold rents below market to reward loyalty and create stability, you may unintentionally anchor tenants in place, limiting their mobility and long-term advancement.

Either way, the outcome is not as clear-cut as we once believed. Julie and I have lived this. We have intentionally left rents unchanged for good tenants, believing we were helping families budget, plan, and build stability. I still believe there is value in that approach. Stability matters. Community matters.

But this new perspective forces us to ask a harder question: are we creating opportunity, or quietly limiting it? The reality is that this is not a problem landlords can solve alone. It is tied to housing supply, interest rates, wage growth, and public policy. But landlords are not bystanders either. We operate on the front lines of these decisions every day.

Perhaps the answer is not choosing one extreme or the other but being more intentional. Understanding why tenants stay. Communicating openly. Creating value beyond rent. And recognizing that what looks like success on a spreadsheet may carry unintended consequences in real life.

Because sometimes in real estate, as in life, you can do everything right and still find yourself in a no-win situation. And that may be the most important insight of all.

Dr. J. David Chapman is the Chair of Finance and Professor of Real Estate at The University of Central Oklahoma (jchapman7@uco.edu)