Stop Missing Deductions! A CPA’s Guide to Real Estate Taxes & Structuring

In this episode of the CRESI Ontario Landlord Series, Kevin sits down with Michael Matthew, a CPA, CA, and experienced real estate investor, to take things back to basics. Whether you are buying your first rental property or looking to optimize your current portfolio, getting the financial structure right from day one is critical. We dive deep into the most common questions new investors face: Should you incorporate or own personally? What expenses are landlords frequently missing? And how do you protect your assets from liability? Michael also shares insights from his book, Eh to Zen Real Estate, and discusses why treating your rentals like a business—not a hobby—is the key to long-term success. In this episode, we cover: The "Personal vs. Corporation" debate: Liability protection vs. tax rates. Understanding Capital Cost Allowance (CCA) and depreciation. The biggest tax deductions landlords often miss. Best practices for bookkeeping and receipt management. Market predictions for Ontario housing supply through 2030. About Our Guest: Michael Matthew is a CPA, CA with over 35 years of experience and a real estate investor who specializes in helping other investors with tax consulting, structuring, and accounting for both Canadian and American properties. Connect with Michael Matthew: Email: [email protected] Book Website: https://ehtozen.ca/ LinkedIn:   / michaeldmatthew   Facebook:   / michael.matthew.146   YouTube:    / @chestertheinvestorshow   Get Michael’s Book: Eh to Zen Real Estate on Amazon: https://www.amazon.ca/Eh-Zen-Real-Est... Timestamps: 0:00 - Introduction 2:07 - Getting Started: Personal Name vs. Corporation? 3:31 - Liability Risks: Why you might need a Corp 6:32 - Depreciation (CCA) and Tax Deductions Explained 9:58 - The Most Missed Expenses for Landlords 11:57 - Shoebox vs. Software: Organizing Your Receipts 14:32 - Incorporation Deep Dive: Controlling Income Timing 20:11 - Should You Hire Property Management? 22:49 - Eh to Zen Real Estate: Strategies for Peace of Mind 26:24 - The #1 "Do" and "Don't" for New Investors 29:39 - Rent Increases & The "Hobby" Trap 31:21 - Market Outlook: Supply Shortages & Future Pricing 34:13 - Conclusion Disclaimer: This podcast is for informational and entertainment purposes only. Advice shared may not apply to your unique situation. Always seek personalized advice from a qualified professional before making any investment decisions.