Becoming a Property Investor: Decisions for the First-Time Landlord

In July 2025, Alexa Stone was multitasking. It had been just a few weeks since she had packed up her downtown Chicago condo and shipped her belongings to New York City, where she had recently accepted a position as a senior risk analytics manager for a major insurance company. Rather than sell her Chicago condo, Alexa had decided to lease it out to earn some extra income. During these past few weeks, she had conducted market research, prepared the unit for rent, and gathered applications for prospective tenants. She still needed to select who would be her first tenant, as well as to consider whether she was adequately prepared to become a landlord.