The Cleveland Real Estate Investor

Magic Matching Day

Reilly Properties Episode 103

In this episode of Cleveland Real Estate Investor, Mike, Brook, and A'marri discuss Match Day, when medical school graduates are placed in residency programs and begin searching for rental housing. This presents a great opportunity for landlords to secure responsible, long-term tenants—young doctors who are focused on their work and need stable housing.
They also explore the changing nature of the rental market, as Airbnb has become oversaturated, with nearly every Tom, Dick, and Harry trying to become a host. With short-term rentals losing profitability, the team discusses shifting to a rental model that falls between Airbnb and traditional long-term leasing. Tune in for insights on how to adapt to these shifts and maximize rental income.
1:30 Brook explains how they analyze their real estate portfolio, deciding which properties are profitable and which ones should be sold.
3:00 Mike shares the backstory of how they got into real estate, starting with their first rental property and transitioning from house flipping to short-term rentals.
5:00 The team discusses the shift away from short-term rentals due to market saturation and why midterm rentals for medical residents on Match Day present a great opportunity.
10:30 Mike emphasizes the importance of tenant screening, explaining why credit scores matter and how bad tenants can lead to financial and property damage.
19:00 A'marri and Brook highlight key rental strategies, including lease structuring and pricing for different rental durations to maximize returns.