The Question That Can Make or Break Your Next Rental Deal

August 7, 2025

The Make-or- Break Question for Wise Landlords

Every investor looks at numbers. But the smartest ones also look at livability.

Before you buy your next rental property, ask yourself this:

Would I live in this rental?

Not would you want to live there. That’s different.
Not whether it has your dream kitchen or backyard firepit.
But if you had to move in for a year, could you make it work?

If the answer is no, it’s time to stop and look closer.

Why This One Question Matters So Much

A lot of investors get caught up in spreadsheets. They love the projected ROI, the cap rate, the “cash-on-cash.” And yeah, those numbers matter. A lot.

But there’s a problem.

If the property feels dark, cramped, weird, or rundown... if the street is loud, unsafe, or isolated... if the layout makes zero sense or the place has a strange smell baked into the walls, then the numbers don’t mean much.

Because a tenant still has to want to live there.

Livability Drives Everything Downstream

Here’s what we’ve seen over the years:

Homes that feel clean and comfortable rent faster
They attract better-quality tenants
They stay occupied longer
They generate fewer complaints
They take less wear and tear
And they hold value better over time

When a rental feels like somewhere someone could actually enjoy living, you cut out 80 percent of the friction that comes with landlording.

You don’t have to offer luxury.
But you do need to offer dignity.

Red Flags We Watch For

When we walk a property with a client, here are a few red flags that signal “bad fit,” even if the numbers look good:

The windows are small and the rooms feel gloomy
There’s an odd smell you can’t quite place
You walk in and instantly feel cramped or disoriented
The street has too much traffic or not enough lighting
There’s a long list of deferred maintenance you can see
The neighbors’ properties are in rough shape
Or worst of all: your gut says “this doesn’t feel right”

You don’t have to run from every imperfection, but you do need to notice the big picture. Livability is about the whole experience, not just rent per square foot.

Real Example: The Duplex That Looked Great on Paper

A client came to us with a duplex that had what looked like perfect numbers. Each side rented for $1,600. The mortgage would be $2,100. Insurance and taxes came to $400. Cash flow looked solid.

But when we visited, it was a different story.

The street was noisy, right next to a tire shop. The units were dark and smelled like old smoke. The layout had both bedrooms in the basement. There were no closets. And the backyard had a broken fence and cracked patio.

Could you technically rent it out? Yes.
Would people be excited to live there? Not likely.

Our advice: keep looking.

That investor waited three months, found another duplex with smaller numbers but way better feel, and now has tenants who signed two-year leases and treat the place like their own.

Sometimes the safer bet isn’t the one with the highest upside. It’s the one with fewer headaches.

What Livability Actually Looks Like

You don’t need granite counters. But you do want:

A layout that flows
Natural light in main rooms
A kitchen people can actually cook in
A neighborhood people feel safe walking at night
Close access to groceries, jobs, or transit
A clean, well-maintained feel, even if the materials are basic

Livability is the difference between short-term tenants and long-term ones. Between someone who moves out after one lease and someone who stays for years.