The Globetrotting Investor: Navigating the Complexities of Cross-Border Wealth

As more Canadians pursue opportunities abroad—whether it’s purchasing a villa in Portugal, a beach house in Italy, or investment property in Israel or the U.S. - advisors are increasingly being called upon to manage the tax and compliance challenges that follow. Capital is mobile, but taxes are not, and the complexity of cross-border investment planning has never been greater. That’s why the CE Savvy Summit on September 17, 2025 will feature a timely session, The Globetrotting Investor, led by Dr. Dean Smith, PhD, CFP, TEP, CPA, CA, RWM™, FDFS™, to help advisors navigate these growing challenges with confidence.

Understanding the Tax Compliance Burden

Owning foreign investments raises numerous compliance questions. Advisors need to understand how to correctly report these holdings, calculate foreign exchange gains, and address withholding tax issues that can significantly erode returns if not properly managed. Even the handling of financial T slips introduces complexity, creating additional costs and risks of error at tax filing time.

Audit risk is also heightened. With the CRA expanding its ability to analyze global data, advisors must ensure clients are not only compliant but also well-prepared should scrutiny arise. This means knowing how to identify potential red flags, mitigate exposure, and provide strong audit defence when required.

Cross-Border Inheritance and Estate Planning

The inheritance of foreign property introduces another layer of complication. Civil and common law systems differ greatly, and without careful planning, families may face unexpected taxes, delays, and disputes. Dr. Smith will highlight how trusts, tax treaties, and thoughtful structuring can be used to preserve wealth across borders, especially when family members reside in different jurisdictions.

Practical Filing Insights

In addition to estate and compliance considerations, Dr. Smith will explore the practical aspects of filing Section 216/217 returns for non-resident partners in real estate, calculating the correct amount of tax withheld, and obtaining Certificates of Clearance upon the sale of Canadian assets. These technical insights are essential tools for advisors working with clients whose investments cross borders.

Why This Matters Now

Global investment is no longer the exception—it’s quickly becoming the rule among affluent Canadians seeking diversification, lifestyle options, or business opportunities abroad. Advisors who can confidently address the tax and legal implications of international holdings will be better positioned to strengthen client trust and deliver real value in an increasingly complex environment.

The Globetrotting Investor session at the CE Savvy Summit on September 17, 2025 is a timely opportunity for financial professionals to deepen their expertise in cross-border planning and compliance, ensuring they are prepared to guide clients through the challenges and opportunities of global wealth.

Register online by Sept. 10 for early-bird savings. Group rates available! Can’t attend live? The session recordings will be available!