What to Look for in a Property Management Company: A Landlord’s Guide to Getting It Right

As a landlord, hiring the right property management company can be one of the most important decisions you make. Whether you own a single-family rental or a multifamily unit in Washington D.C., the person (or team) managing your property will impact your cash flow, tenant experience, and long-term equity. This isn’t like working with a typical real estate agent. A property manager is in your life regularly, solving problems, answering tenant calls, and protecting your investment day in and day out.

As someone who owns a multifamily property in D.C. myself, I’ve lived through the stress of being overwhelmed. I know what it feels like to want to walk away from the whole business, and I almost did. But once I worked through the challenges, something clicked: I realized I could help other landlords avoid the same mistakes and burnout.

So trust me when I say: choosing the right property manager matters.

Questions Landlords Should Ask Before Hiring a Property Manager

Here are a few questions to ask when interviewing any property management company (even if it’s not us):

1. How often will I hear from you?

   • Look for transparency and regular communication. A good manager doesn’t just reach out when there’s a crisis.

2. Who will be my main point of contact?

   • Some companies pass you around. You want someone who knows your property — not just your account number.

3. How do you handle maintenance requests?

   • Find out how repairs are tracked, approved, and communicated. Regular maintenance isn’t just a cost, it protects your property’s value.

4. What’s your fee structure?

   • Make sure you understand not just the monthly fee, but also leasing fees, renewal fees, and any markups on maintenance.

5. How do you handle problem tenants or late rent?

   • You need someone who will be firm but fair, and proactive when things go wrong.

6. Do your values align with mine?

   • This one’s harder to quantify, but maybe the most important. Do they care? Will they treat your property like it’s their own?

   
   

   

   When interviewing property management companies to make sure they are the write fit, stay organized by writing out the responses to review later.

   
   
   
   

A Few Tips for Choosing the Right Fit

✔️ Prioritize communication. Property management is a relationship. If your manager goes silent when things get tough, you’ll be left dealing with stress you’re paying them to handle.

✔️ Check for local expertise. You want someone who knows the ins and outs of your city or neighborhood — especially in D.C. where regulations can be complex.

✔️ Look beyond the sales pitch. Big companies might have polished websites and fancy dashboards, but that doesn’t mean they’ll remember your name — or the color of your front door. Sometimes smaller, hands-on firms provide better service because you matter more to them.

✔️ Ask for real-world examples. How have they handled a tough tenant situation? How did they improve cash flow or reduce vacancy for a past client?

Why This Is So Personal for Me

When I first bought my investment property in Southeast D.C., I was thrilled. I remember standing on the front steps, feeling like I had just opened the door to a whole new chapter. I was finally stepping into real estate, building equity, generating cash flow, and creating long-term wealth. But that initial excitement quickly turned into stress, fear, and a whole lot of hard lessons.

Months after closing, I discovered a serious mold issue in the house, one that had gone unnoticed during the buying process. What started as a dream investment suddenly became a financial and emotional burden. I was making late-night calls trying to find contractors for mold remediation, struggling to coordinate quotes, and navigating repairs I never saw coming. On top of the mold, I had to repoint bricks on the exterior walls because moisture was leaking in from outside. Then came drywall replacement. More contractors. More costs. More delays.

It felt endless. I was overwhelmed, underprepared, and completely drained. I spent thousands of dollars, money I hadn’t planned to spend, and at one point, I seriously considered walking away from real estate altogether. What I had set out to do financially wasn’t happening the way I’d envisioned. I had to make it happen, and that meant stepping back, re-strategizing, and approaching the business of being a landlord in a completely new way.

That experience nearly broke me (and the bank) but it also changed everything.

I learned how to vet contractors, how to gather quotes strategically, and how to avoid being taken advantage of. I learned what it really means to take care of a property, and just how costly it can be when you don’t. And I saw firsthand how easy it is to get in over your head when you don’t have the right support.

That’s why I do what I do today. That’s why this business is so deeply personal to me.

Because I’ve lived the hardest parts of property ownership, I know what it takes to manage a home, and I also know how to help other landlords recover from similar challenges or, even better, prevent them entirely. Things like choosing the wrong tenant? Costly. Skipping regular maintenance? Even more costly down the line. Being reactive instead of proactive? It chips away at your equity, your cash flow, and your peace of mind.

At Greenway Capital Properties, I bring that experience into every client relationship. I know that communication is everything, not just when things are going smoothly, but especially when they’re not. Property management isn’t a hands-off relationship. It’s collaborative. It’s frequent. We talk often. We problem-solve together. And that means our values need to align.

This isn’t just about numbers or percentages. This is about people. Your property might be one of your biggest investments, and you deserve a manager who treats it with that level of care. Someone who doesn't just know how to manage maintenance requests, but who understands the weight of that responsibility.

That’s why I show up the way I do. Because I’ve been there. And I want my clients to know: you don’t have to go through it alone.

A furnished home in NW D.C. managed by Greenway.

Final Thoughts

Choosing the right property manager isn’t just about price — it’s about trust, alignment, and results. Whether you work with Greenway Management or not, I hope you find someone who cares as much about your property as you do. And if you’re still figuring it out? Let’s talk. I’d love to hear about your property, your goals, and how we can build a plan that works for you.