In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Rhys Wyn Trenhaile, broker and team leader of The Vanguard Team at Manor Windsor Realty Ltd. in Windsor, Ontario. Rhys shares his unique path from being a national championship-winning track and field athlete at the University of Windsor to becoming a seasoned real estate investor and broker. Starting in university, he and his teammates dove into student rentals during long training runs, sparking a passion for landlording that led to owning multiple properties early on. After earning a law degree but opting out of practicing due to low starting salaries, Rhys transitioned into real estate, leveraging his investor mindset to build a successful career over 21 years.

Rhys emphasizes the importance of working with agents who invest themselves, highlighting how his team practices what they preach—converting active income into passive wealth through properties. He discusses Windsor's evolving market, noting streamlined permitting processes via cloud systems and development coordinators, which have halved approval times from two years to one. With major projects like converting downtown buildings (including the 67-unit Canada Building) into residential spaces, Rhys points to government incentives for conversions and infill developments. As of November 2025, Windsor's real estate market remains stable with an average home price around $544,657, down slightly from previous months amid increased listings and modest sales declines, driven by infrastructure like the Gordie Howe International Bridge and ongoing population growth projections of 31% in Southwestern Ontario by 2051.

The conversation covers practical investing strategies, from overcoming mental barriers for first-time buyers to using the BRRRR method (Buy, Renovate, Rent, Refinance, Repeat) for scaling portfolios. Rhys advises on additional dwelling units (ADUs) like mother-in-law suites for cash flow without traditional duplex limitations, and warns against most condos for investments, identifying only a few viable options out of hundreds. He stresses long-term relationships over quick sales, noting how his team's honesty and expertise have led clients to retirement wealth. This episode provides actionable insights for investors in Ontario's commercial and residential scenes, blending personal anecdotes with verified market trends for building sustainable wealth.

Key Takeaways

• Early Investing Spark: While running track at university, Rhys and teammates bought student rentals, leading to national championships in 1998 and early wealth-building through real estate.
• Career Pivot to Real Estate: After law school, Rhys chose real estate over low-paying legal jobs, using transferable skills and personal investments to guide clients effectively.
• Mindset for New Investors: The first property is toughest due to fear; focus on calculated risks, and by the third, steals become recognizable with experience and team support.
• BRRRR Strategy: Buy undervalued homes, renovate for ADUs like basement suites, rent for cash flow over $1,000/month, refinance to pull out capital, and repeat for portfolio growth.
• Windsor Market Update 2025: Average prices stabilized at ~$544,657 in November 2025 with slight declines and more listings; growth fueled by infrastructure, population influx, and easier permitting.
• Government Incentives: Federal pre-approved sixplex designs bypass local bureaucracy; provincial fourplexes as-of-right in many areas; CMHC financing up to 95% for multi-units.
• Client-Centric Approach: Avoid junk properties for long-term success; team greed aligns with client wealth—more buys mean more commissions for their own investments.
• Condo Caution: Out of 179 condos, only three are strong investments; prioritize well-managed buildings for professionals seeking steady, low-maintenance returns.

Links to Show References

• Rhys Wyn Trenhaile's Contact: Phone - (519) 250-8800; Email - rhys@manorrealty.ca; Website - thevanguardteam.com; Instagram - @rhystrenhaile
• LendCity Mortgages (for Pre-Approvals and Investment Financing): lendcity.ca
• Manor Windsor Realty Ltd. Office: 3276 Walker Road, Windsor, Ontario for consultations
• YouTube Channel for More Insights: Search "The Vanguard Team Windsor"

• (00:04 ) - Welcome to the Wisdom Lifestyle Money Show


• (02:03 ) - Journey into Commercial Real Estate


• (05:03 ) - Transitioning from Law to Real Estate


• (10:07 ) - Understanding Investor Mindset


• (15:09 ) - Honest Conversations About Investing


• (19:23 ) - Future Topics and Next Steps

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