From Accidental Investor to Mortgage Expert: Gillian Irving's Real Estate Story

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham chats with Gillian Irving, a mortgage agent at LendCity specializing in investment properties and student rentals. Gillian shares her journey as an "accidental investor," starting in 2008 after reading Rich Dad Poor Dad. She bought her first property in Toronto's Leslieville neighborhood on a whim, refinancing it multiple times to fund expansions into student rentals in Hamilton, Ontario. Drawing from her experiences, she discusses how real estate investing transformed her life, emphasizing the power of appreciation, mortgage paydown, and cash flow. Gillian also highlights transferable skills from her background and offers insights into overcoming initial fears, especially with the first property being the hardest due to potential vacancies.

Post-COVID, Gillian notes shifts in the student rental market. While demand surged initially leading to higher rents, recent 2025 data shows rents easing due to federal caps on international students, with Hamilton's median rent at around $1,850 in November 2025, down slightly year-over-year. Vacancy rates are rising nationally, but opportunities remain in underserved areas near universities like McMaster. She debunks myths about student tenants causing damage, stressing the use of parent guarantors for security. Financing remains challenging, with fewer lenders offering options for refinances and purchases of existing student rentals, often requiring 20-35% down payments. However, major banks may approve if the property is owner-occupied by a student child, and commercial lending provides paths to scale beyond residential limits.

Looking ahead, Gillian reveals her new strategy: investing in four-season cottage rentals in Ontario, designed to be recession-proof amid economic uncertainty. With more families opting for affordable staycations over international travel, these properties—featuring year-round activities like skiing in winter and boating in summer—cater to shared vacations for multiple families. As of November 2025, Ontario's cottage market shows increased listings and softer prices, boosting rental demand for value-driven getaways. This episode blends personal anecdotes with practical advice for aspiring investors, updated with current market trends for building wealth through real estate in Canada.