Ever wondered what it takes to navigate Philadelphia's complex real estate landscape as a landlord? Sheryl Sitman, founder of Philadelphia Landlords Connect and Real Landlording, offers a refreshing perspective on the challenges and opportunities facing property owners in the City of Brotherly Love.
Sheryl's journey began during the 2009 market downturn, seeking "headache-free" investments before diving into distressed properties in Philadelphia. Like many new investors, she learned painful lessons from costly mistakes and predatory contractors – experiences that fueled her mission to create solutions for other landlords.
When COVID's eviction moratorium threatened landlords' livelihoods, Sheryl built a community that has grown to nearly 3,000 members who help each other navigate Philly's regulatory maze. Unlike other markets where you can simply buy property and rent it out, Philadelphia landlords must obtain rental licenses, lead certifications, rental suitability certificates, and more – creating significant barriers to entry and diverting resources from property improvements.
The disconnect between policymakers and housing economics creates further challenges. Recent proposals to cap rental application fees below the actual cost of credit checks and require security deposits in installments demonstrate fundamental misunderstandings of landlording realities. Meanwhile, thousands of vacant lots owned by the Philadelphia Housing Authority sit unused while potential buyers face insurmountable barriers to purchasing and developing them.
To address these issues, Sheryl is launching a comprehensive website through Real Landlording, designed to support property owners at every stage of their journey. Her goal? Create win-win scenarios where landlords can operate efficiently while properly maintaining their properties and keeping rents reasonable.
"What's good for landlords is usually good for tenants as well," Sheryl emphasizes, challenging the false narrative of landlord-tenant conflict that often dominates policy discussions.
Tune in to hear how successful real estate investing creates freedom to design the lifestyle you want, and discover practical insights for navigating Philadelphia's unique real estate environment.

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