Sheryl Sitman

I built a real estate portfolio that supports my lifestyle, gives me freedom over our time, and creates generational wealth for my kids — and it all started with a single property back in 2009 (before I even moved to the U.S.!). After seeing the upside of that first deal, I knew real estate investing was the long game I wanted to play. I eventually came back to my hometown of Philadelphia and went all in — scaling our portfolio across Pennsylvania and into Florida, the Carolinas, and Texas as part of our early retirement strategy. With efficient systems in place and the right people around me, I’ve gained full control over my time (and let’s just say my frequent flyer miles agree). Today, I run Philadelphia Landlords Connect — the largest and most engaged Facebook community of independent landlords in the region. The group is powered by Real Landlording LLC, a platform helping landlords make faster, smart, profitable decisions at every stage of ownership. Real Landlording is built to fill the gaps I got tripped up on when I was starting out. We offer free tools and solutions that simplify everything from executing a big renovation to managing tenant turnover efficiently. Whether you’re appealing property taxes, in need of reliable contractors, or just want clarity before buying your next property, we’ve got vetted solutions. A few of the tools and services already live on RealLandlording.com: Find a Pro – a vetted referral network to connect landlords with skilled, trustworthy contractors and service providers Scope Assist – a pre-rehab walkthrough + scope and budget range to help investors make smarter purchase and bidding decisions Tax Appeal Support – property-specific guidance and data to help challenge over-assessments Tenant Turnover Toolkit – step-by-step systems and resources to manage turnover efficiently and affordably Preventative Maintenance – to reduce surprises and expenses and keep your properties running smoothly I also host a podcast focused on sharing actionable insights, real talk, and smarter strategies for rental property owners. My mission is to help fellow landlords avoid the expensive lessons and wasted time that so many of us have been through — and instead, channel their energy into better properties, better returns, and more freedom.