From The Scaling Station Podcast — MasterKey’s Blueprint for Successful Property Management in Raleigh

Show: The Scaling Station Podcast with Will Rodowski

Guest: Robert Dell’Osso, CEO & Principal Property Manager, MasterKey Property Management

Full Scaling Station Podcast: From 35 to 500 Doors: MasterKey’s Local Advantage | Robert Dell’Osso, MasterKey | ScalingStationPod

Our very own Robert Dell’Osso recently joined the Scaling Station Podcast to talk about what it really takes to succeed as a rental property investor in today’s market. From growing MasterKey into one of the Triangle’s most trusted long-term property management firms to helping investors make smarter, more profitable decisions, Robert shares practical insights you won’t want to miss.

Highlights from the Conversation

1) How did you get started in property management?

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Family Rentals to Founding MasterKey

Robert grew up helping his parents manage rentals, learning early the value of hands-on work and quality upkeep. After moving to Raleigh in 2000, he launched MasterKey in 2016 to serve intentional, portfolio-minded investors. Today, we manage 500+ investment properties across the Triangle with a professional, tech-enabled team.

Why it matters: Clear processes, consistent standards, and transparent communication protect long-term returns.

2) What do you envision for MasterKey over the next 12 months?

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Growth Is a Goal for the Next 12 Months

Robert names growth as one of MasterKey’s priorities—adding the right doors in the Raleigh/Triangle market while protecting service quality. The focus is on attracting intentional investors, strengthening broker/referral partnerships, and improving organic reach so we bring in more of the ideal owner.

Why it matters: Growth is paced and data-driven—never “growth at any cost.”

3) Why did you start an in-house Maintenance Team for MasterKey?

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Why Maintenance Matters

One of the biggest drivers of ROI isn’t rent growth—it’s tenant retention. With an in-house Maintenance Team, we control quality and scheduling, resolve issues faster, and reduce vacancy. When a property is well-maintained, residents stay longer and turnover costs drop.

“Maintenance directly contributes to minimizing turnover. Nobody makes money when a property is sitting vacant.”

4) What advice do you give investors about choosing the right rental property in Raleigh?

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Coaching Investors on Smarter Buys

We advise many out-of-state investors before they buy in Raleigh. The guidance is simple: prioritize cash flow and durability over sticker price. Instead of one ~$700K property renting for ~$2,200/month, two ~$350K properties each generating ~$1,800/month often deliver better cash flow, diversify risk, and create steadier income.

Why it matters: The right asset mix can materially improve portfolio performance over time.

5) How are current market conditions influencing your rent pricing strategies?

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Staying Competitive in Today’s Market

Rent growth has cooled, and days on market have lengthened in many sub-markets. Rather than pushing residents out with 10–15% hikes, we coach owners to use data-driven, moderate renewals (often 2–5%) that retain reliable residents and avoid expensive turnover.

Why it matters: A measured renewal strategy can save thousands in vacancy and make-ready costs.

6) Does MasterKey hold the same make-ready standards across all rental price points, and what if an owner refuses the work needed?

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Setting Standards Before Listing

Every property—whether a $1,000/month or $5,000/month rental—must meet the same clean, safe, well-maintained standard before listing. If a property won’t meet those standards, we won’t market it. Cutting corners raises vacancy risk, hurts brand reputation, and attracts the wrong applications.

Why it matters: Consistent make-ready standards protect days-to-lease, resident experience, and owner ROI.

7) Why do you consider NC landlord- and tenant-fair, and how does it compare to other states?

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North Carolina’s “Landlord- and Tenant-Fair” Process

Robert walks through North Carolina’s typical nonpayment process and why he views it as balanced: clear notice, a predictable timeline, and due process—without year-long delays. The goal isn’t rushing to court; it’s predictability so owners can plan and residents understand expectations. (General information only; not legal advice.)

Why it matters: Policy stability helps investors and supports a healthy rental market.

8) How does MasterKey’s approach to communication and owner relationships differ from large national firms?

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Why Local, Personalized Service Beats National PM Companies

With MasterKey, owners know exactly who they’re working with—no generic inboxes or call-center runaround. Direct access, up to and including leadership, means faster decisions and accountability.

Why it matters: Local expertise and named contacts reduce friction and protect outcomes.

“We manage properties as if they were our own—because that’s what investors deserve.” — Robert Dell’Osso, CEO, MasterKey Property Management

Listen to the Full Episode

Want the full conversation? Watch Robert’s complete interview with Will Rodowski on the Scaling Station Podcast.
Full episode: https://youtu.be/GZrGojdTVdI?feature=shared