I recently welcomed new client, Gerry A. Scott CIM®, CFP® CRPC® who has just released his guidebook for Canadians living part of the year in the US, owning homes, etc., titled Canadians Heading South for the Winters!
Gerry, (pictured below) has worked in wealth management for 35 years and over the past decade, has become one of Canada’s leading experts in cross-border residency and tax issues.
I sat down for a chat with Gerry so I can share with you the importance of understanding the various challenges being a snowbird entails.
What first prompted you to write this book targeting the “snowbird” community?
A. After more than three decades advising clients—many of whom spend significant time in the U.S.—I kept seeing the same costly mistakes repeated over and over. These weren’t small issues either; they involved taxes, residency status, healthcare coverage, and even being denied entry at the border. Through my work and the Snowbirds Expat Radio Podcast, it became clear there was a major gap between what people think they know and what actually matters. The book was written to close that gap—to provide clear, practical guidance so Canadians heading south can avoid mistakes that can be financially and emotionally damaging.
You’ve been providing wealth management advice for this community for many years—how have all the rules & regulations changed over time? How difficult is it now to own property in the U.S. and travel freely across the border?
A. The biggest shift has been increased enforcement and data tracking. It’s not necessarily that the rules themselves have drastically changed—it’s that governments now have much better systems to monitor and enforce them.
Cross-border travel is far more scrutinized today. U.S. Customs tracks entries and exits electronically, and the IRS applies formulas like the Substantial Presence Test, which can unexpectedly classify Canadians as U.S. tax residents.
Owning property in the U.S. is still very doable, but it comes with more complexity – tax filings, estate considerations, and currency planning all need to be handled properly. The days of casually spending winters in the U.S. without understanding the rules are long gone. 
Are there any specific issues that snowbirds need to address immediately?
A. Absolutely—there are a few that require immediate attention:
- Tracking your days in the U.S. – This is critical. Losing track can trigger U.S. tax residency.
- Filing the right forms – Many Canadians don’t realize they may need to file IRS Form 8840 to avoid being treated as a U.S. resident.
- Healthcare coverage – Provincial coverage has limits, and travel insurance must align with your actual time out of country.
- Estate planning – Owning U.S. assets can expose Canadians to U.S. estate tax if not structured properly.
These are not “nice to have” items—they are essential to get right. 
Prior to your book, you had already introduced an app that allows Canadians to monitor the time (days) allowed in the U.S – how important is that?
A. It’s extremely important – arguably one of the most critical tools a snowbird can use. The rules around how many days you can spend in the U.S. aren’t as simple as just staying under 183 days in a single year. The IRS uses a rolling three-year formula, which can catch people off guard.Check the app for details: @snowbirdstrackerapp
About the Author:
Gerald A. Scott CIM®, CFP® CRPC® is a cross-border financial professional and educator focused on issues affecting Canadian snowbirds and expatriates. He is also the founder of tools and resources created to help Canadians better track time in the U.S. and make more informed cross-border decisions. Through his work, Gerry has helped shine a light on the practical realities snowbirds face when navigating life between Canada and the United States. Gerry is currently working on his second book.
He’s spent 35 years—and counting—in the wealth management world. Over the last decade, my work has focused almost entirely on the cross-border space. He holds portfolio management licences in both Canada and the United States, and he’s fully designated to write comprehensive financial plans for Canadians who spend part of the year in the United States, including Snowbirds and individuals navigating cross-border tax and residency considerations related to extended winter stays. This book has grown out of that work.
The book is available now from Amazon so if you are a snowbird…or as we call ’em Down Under, grey nomads, this is an essential travel companion! Here’s the direct link for your convenience: https://bit.ly/4tfQk4Y
You can follow the “snowbird trail” with Gerry on social media @snowbirdsusdaytracker.