Building a successful real estate portfolio from the ground up isn’t easy, but as Ali and Josh Lupo have shown, it’s possible with consistency, commitment, and purpose.
Ali and Josh Lupo are a married couple and real estate investment duo with years of experience in property management. In this Q&A, they share their top tips and tricks for building a successful rental business, along with their favorite ways to utilize the Apartments.com Rental Manager platform for vital landlord tasks.
When did you begin managing rental properties? Why? What made you start?
We bought our first duplex in 2018. At the time, we were newlyweds. We were searching for a creative way to reduce our cost of living, and real estate became the tool that helped us build a more secure financial future for our family.
What is your favorite part about managing rental properties?
Honestly, it’s twofold: seeing a family move into a safe, clean, affordable home and knowing we’re supporting our community by giving love and TLC to older homes that need it. It's also incredibly rewarding to watch our properties generate income that gives us more time with our daughter. It’s a win-win for both our tenants and our family.
What has made you successful in property management?
We genuinely care. We treat our tenants like people, not just transactions. We’re responsive, keep our properties in great condition, and communicate clearly. That, combined with a mindset of always learning and improving, has helped us build strong relationships and long-term success.
What are some challenges you've faced as landlords?
We’ve had our fair share of late-night maintenance calls and off-season turnovers. We’ve also experienced those seasons where everything seems to hit at once—multiple repairs, unexpected expenses, and lots of moving parts. But every challenge has taught us something valuable and helped us become more resilient, efficient, and proactive as landlords.
What specific tools within Rental Manager do you find most helpful and why?
We’ve found the tenant screening and listing features especially helpful. Being able to easily list a property, reach qualified applicants, and screen tenants in one place streamlines the process and helps us find great fits for our rentals with less stress.
Why is it important to you to use a rental property management tool like Apartments.com?
When you’re managing multiple units and wearing many hats—as landlords, business owners, and parents—efficiency matters. We’re all about tools that help us stay organized and professional while saving time and giving us the ability to scale with confidence.
What’s your number one tip for someone starting their property management business?
Start small. Stay consistent. And treat your rental like a real business from day one. Put strong systems in place early and always remember—it’s a people-first business. The way you treat your tenants, partners, and yourself matters more than you think.
