In this episode of the Snowbirds Expat Radio, host Gerry Scott welcomes back cross border tax specialist Sharon Conrod of Hanson Tax LLC for a timely conversation on one of the most misunderstood cross border situations today Canadians living in Canada while working for U.S. employers.

As more professionals take U.S. roles while residing north of the border questions around 401k plans IRAs RRSP room and treaty relief are becoming increasingly common and increasingly complex. Sharon explains how U.S. retirement plans are treated in Canada when deductions are available why tracking basis matters and where many people unknowingly create future tax issues.

The discussion also explores remote work considerations employer matching crystallization strategies state level tax risks and why there is truly no one size fits all solution when families live and work across borders.

What You Will Learn

• How 401k and IRA contributions are treated when you live in Canada

• When U.S. retirement contributions may or may not be deductible in Canada

• Why RRSP room limits matter for cross border commuters

• The role of Form RC268 and why it is critical for Canadians with U.S. plans

• How employer matching works and when it still makes sense to participate

• Why tracking non deductible contributions over time is important

• How crystallizing RRSPs before moving to the U.S. can reduce future taxes

• Why certain U.S. states can complicate otherwise treaty protected plans

• Common mistakes remote workers and employers make

• Why residency and family dynamics matter in cross border planning

Why This Episode MattersCross border work arrangements have grown significantly but the tax rules have not become any simpler. This episode highlights why working with experienced cross border professionals can help prevent costly mistakes both now and in the future.

In this episode of the Snowbirds Expat Radio Podcast, host Gerry Scott welcomes back returning guest Aaron Dawes, a cross-border personal tax expert with Smythe.

While previous conversations focused on Canadians heading south, this discussion flips the script. With shifting economic, political, and lifestyle factors, more Canadians—and Americans—are now moving north, returning to or relocating to Canada despite weather, cost, and lifestyle tradeoffs.

Aaron explains what’s driving this trend and what individuals need to consider before making the move, especially when it comes to cross-border tax exposure.

In this conversation, Gerry and Aaron discuss:

• Why more Canadians are returning home from the U.S.

• What’s motivating Americans to relocate to Canada

• How lifestyle, stability, and long-term planning factor into relocation decisions

• The tax implications of moving between the U.S. and Canada

• Why cross-border tax planning is critical before you move

• Common mistakes people make when changing tax residency

• How working with a specialist can prevent costly surprises

With decades of experience handling U.S.–Canada personal tax matters, Aaron offers practical insights for snowbirds, expats, and globally mobile families navigating an increasingly complex cross-border landscape.

If you’re considering a move—or a move back—this episode highlights why planning ahead matters more than ever.

Spending time in the U.S.? Take the guesswork out of tracking your days. Download the Snowbirds U.S. Day Tracker app to monitor your stays, stay compliant, and avoid costly surprises at the border.

Connect with Aaron Dawes

What does it really mean to leave Canada — and how do you know when you’ve crossed the line from spending time abroad to officially exiting?

Host Gerry Scott sits down with Jennifer Reid CPA, CGA, TEP and Frank Casciaro of RSM, two cross-border tax specialists who advise Canadians navigating complex international lives — from snowbirds and dual citizens to executives, business owners, and globally mobile families.

With deep experience in international tax and firsthand insight from working with clients before, during, and after a Canadian exit, Jen and Frank break down why leaving Canada is not just a lifestyle decision — it determines how your assets are taxed, what reporting obligations follow you, and where costly compliance mistakes often happen.

Together, Gerry, Jen, and Frank unpack the realities behind some of the most misunderstood rules in Canadian departure planning, including why residency is rarely as simple as counting days or keeping a Canadian mailing address.

In this conversation, they explore:

• Why more than 106,000 Canadians left the country in 2025 — and what’s driving the trend

• The difference between being a factual resident and a non-resident of Canada

• Why spending a few months abroad doesn’t automatically mean you’ve exited

• What departure tax and “deemed disposition” really mean in practice

• Which assets are subject to departure tax — including worldwide holdings, not just Canadian ones

• When deferring departure tax may be possible, and why it’s becoming harder to do

• How the Canada–U.S. tax treaty can help prevent double taxation — and where it falls short

• Why health care eligibility (including OHIP) is not tied to your tax return

• The compliance risks of keeping Canadian bank accounts, investments, or a family address after leaving

• TFSA, RRSP, and withholding tax issues that frequently catch departing Canadians off guard

• Why planning before you leave is far less expensive than fixing mistakes afterward

If you’re living, working, retiring, or investing outside Canada — or considering a permanent move — this episode offers a clear, practical look at what truly defines a Canadian exit and the planning steps that can save you from expensive surprises down the road.

What does it really mean to be a tax resident — and why do so many people accidentally get it wrong when moving between Canada and the United States?

Host Gerry Scott sits down with Nicole Madaisky, a dual-licensed Canadian and U.S. CPA who specializes in complex cross-border lives — from snowbirds and dual citizens to professional athletes and globally mobile families.

With deep experience in international tax and firsthand insight from working with clients on both sides of the border, Nicole breaks down why tax residency is not just a formality — it determines who gets to tax you, how much you owe, and where costly mistakes often happen.

Together, Gerry and Nicole unpack the realities behind some of the most misunderstood rules in cross-border tax planning, including why residency is rarely as simple as counting days or holding a passport.

In this conversation, they explore:

• Why tax residency — not citizenship — often determines which country can tax your worldwide income

• How Canada’s primary and secondary residential ties actually work in practice

• Why the 183-day rule is frequently misunderstood and rarely tells the whole story

• The common ways Americans and Canadians unintentionally trigger tax residency without realizing it

• What snowbirds need to understand about time tracking, treaty rules, and U.S. exposure

• Why buying property in Canada too early can create long-term tax and compliance issues

• How Canadian mutual funds can become a serious problem for U.S. taxpayers

• The foreign reporting requirements that carry steep penalties when overlooked

• Why cross-border planning works best when accountants, advisors, and immigration professionals work as a coordinated team

If you’re living, working, retiring, or even just spending extended time between Canada and the U.S., this episode offers a clear, practical look at the rules that matter most — and the planning steps that can save you from expensive surprises down the road.

Get In touch with Nicole: https://www.nicolemadaiskycpa.com/

Spending time in the U.S.? Take the guesswork out of tracking your days. Download the Snowbirds U.S. Day Tracker app to monitor your stays, stay compliant, and avoid costly surprises at the border.

In this episode of Snowbirds US Expats Radio Podcast, Gerry Scott speaks with Donnie Arnoult, an avid cyclist, local business owner, and passionate advocate for Maui’s natural beauty.

Donnie is the founder of Maui Cyclery, a well-known bike shop in the town of Pāʻia, and a trusted name in Maui’s cycling community.

With decades of experience riding on and off-road across the island, Donnie always dreamed of creating something more immersive — a way to share the untamed beauty of Maui with both visitors and locals in a sustainable, approachable way.

That dream became reality with Emountain Bike Tour Maui: a guided e-bike experience that allows riders of all levels to explore hidden trails, soak in stunning ocean and volcano views, and encounter local wildlife — all while treading lightly on the land.

Donnie’s deep love for Maui and cycling shines through in every tour. His mission is simple: to connect people with the land through the joy of riding.

Spending time in the U.S.? Take the guesswork out of tracking your days. Download the Snowbirds U.S. Day Tracker app to monitor your stays, stay compliant, and avoid costly surprises at the border.

What actually happens when you try to move between Canada and the United States without a solid immigration plan — and why are so many families getting stuck, delayed, or denied?

In this episode, Gerry Scott sits down with Evelyn Ackah, Founder of Ackah Business Immigration Law, to unpack why pre-immigration planning has become essential for Snowbirds, cross-border families, and professionals navigating life on both sides of the border.

With more than 25 years of experience — and her own personal journey immigrating to Canada — Evelyn brings both expertise and heart to the conversation. She explains how immigration, tax, real estate, and family planning all intersect long before an application is ever filed.

Gerry and Evelyn break down:

• What pre-immigration planning really looks like (and why it saves money, time, and stress)

• How relocating affects tax residency, investments, real estate, and corporate structure

• What Canada’s reduced immigration targets mean for workers, families, and retirees

• The most common mistakes people make when they DIY their immigration using Google or ChatGPT

• Why border officials are showing increased scrutiny, from secondary screenings to Nexus revocations

• New U.S. rules requiring registration for anyone staying 30+ days, including teenagers

• How to navigate life when one spouse is Canadian and the other is American

• Why parents should register their children for Canadian citizenship early to avoid future complications

• What options exist when a spousal PR application is refused — and why reapplying properly often wins

• How business owners and professionals use intercompany transfers to relocate to Canada

• Real-world stories showing how one old border conversation or missed detail can derail an application

Evelyn’s insights make one thing clear: pre-planning isn’t optional anymore — it’s the key to keeping families together, avoiding financial surprises, and crossing borders with confidence.

Connect with Evelyn Ackah:👉 Ackah Business Immigration Law https://www.ackahlaw.com/

Spending time in the U.S.? Take the guesswork out of tracking your days. Download the Snowbirds U.S. Day Tracker app to monitor your stays, stay compliant, and avoid costly surprises at the border.

When professional athletes sign big contracts or executives relocate across borders, the tax implications can be as complex as the game itself. In this episode, Gerry Scott talks with David Silber, Partner at Crowe Soberman LLP, about how athletes and high-income earners structure their finances when moving between Canada and the United States.

David leads the firm’s Sports and Entertainment Division, advising athletes in hockey, baseball, basketball, F1, tennis, golf, and more. He and his team help clients determine tax residency, manage multi-jurisdiction income, and build long-term financial strategies that protect their earnings.

Gerry and David break down:

• How tax residency is actually determined

• What happens when athletes split their time between two countries

• How U.S. and Canadian tax authorities coordinate on cross-border income

• The advantages and limitations of RCAs (Retirement Compensation Arrangements)

• How state-by-state taxation affects athletes playing in the U.S.

• When buying property in Canada helps or hurts an athlete’s tax position

• How departure tax works when leaving Canada

• Why executives recruited from the U.S. face many of the same planning challenges as pro athletes

David also shares insights into signing bonuses, TFSA restrictions for U.S. residents, and why agents increasingly involve tax professionals before deals are finalized.

Connect with David: https://www.linkedin.com/in/david-silber/

https://www.crowe.com/ca/crowesoberman/about-us/our-people/david-silber

Spending time in the U.S.? Take the guesswork out of tracking your days. Download the Snowbirds U.S. Day Tracker app to monitor your stays, stay compliant, and avoid costly surprises at the border.

Can your U.S. vacation home qualify as your principal residence in Canada?

Buying, selling, or co-owning a home across the U.S.–Canada border can create a web of unexpected tax implications — especially when both countries have their own rules about what qualifies as a principal residence.

In this episode, Gerry Scott sits down with Karlene Mulraine, a cross-border tax specialist and founder of Brij Professional Corporation, to unpack how principal residence exemptions work on both sides of the border and how cross-border couples can plan smartly before making property decisions.

Karlene, who recently earned her Master’s in Taxation from Golden Gate University, shares her insights on key filing requirements, capital gains rules, and the 2026 Canadian inclusion rate change that could impact future property sales.

🔍 Key Topics Covered

• 🏡 Principal Residence Rules: How Canada and the U.S. define and tax your main home — and why the details differ.

• 💍 Cross-Border Couples: What happens when a Canadian marries a U.S. citizen and adds them to the property title.

• 💸 Capital Gains & Exemptions: Understanding the $250K/$500K U.S. exclusion versus Canada’s unlimited principal residence exemption.

• 📜 FIRPTA Withholding: What Canadians should expect when selling U.S. real estate and how to reclaim excess tax withheld.

• 🧾 Claiming Foreign Tax Credits: How proper reporting prevents double taxation between the two countries.

• 🔁 Upcoming Rule Changes: How Canada’s 2026 capital gains inclusion rate increase could affect property sales.

• 🌴 Market Trends: Why rising insurance rates, unfavorable exchange rates, and shifting lifestyles are leading more Canadians to sell their U.S. vacation homes.

Visit www.brij.tax to learn more about Bridge Professional Corporation and Karlene’s cross-border tax services.