Advertise on podcast: Snowbirds US Expats Radio Podcast

Moving back to Canada: what happens to your 401(k) and IRA? Gerry Scott, host of Snowbirds Expat Radio, swaps seats for this episode and becomes the guest. His friend ,Toronto Mike, steps into the interviewer role and walks him through Chapter 3 of The Great Return, a guide for Canadians moving home from the US that doubles as a first look at Canada for Americans heading north. The book review series was meant to feature a rotating cast of cross-border specialists, but schedules kept getting in the way, so the author took the chair himself. Chapter 3 is about what happens to your money when you cross the border. Gerry explains why a move home feels simple on paper but carries serious tax and regulatory consequences when the wrong people are advising. He covers the most common mistakes, what happens to 401(k)s, IRAs, and regular US investment accounts once you hold a Canadian address, why timing matters, and what a realistic checklist looks like. He also previews the healthcare coverage gap that returning Canadians can fall into, which gets its own deep dive in Chapter 7. The conversation opens with a short tribute to Canadian rocker Sass Jordan, and Gerry closes by explaining why the show has never been a do it yourself podcast: the right team in front of you matters more than any shortcut. What You’ll Learn Why a move home needs a plan for your money as well as your belongings Why so many people skip planning, and why the instinct to save on professional fees costs more later The most common mistake: taking free advice from friends, family, or an advisor licensed in only one country How RRSPs and TFSAs compare to IRAs and Roth IRAs, why they are not interchangeable, and why the tax treaty has not kept pace with the TFSA Why a US advisor generally cannot keep managing your IRA, 401(k), Roth, or non-registered accounts once your statements show a Canadian address Why borrowing a relative’s US address to get around this backfires How forced cash outs create tax consequences on both sides of the border, and why worldwide income must be reported once you are a Canadian resident How mismatched tax slips and residency records create headaches at filing time Why Gerry suggests planning up to five years ahead, and the three professionals to put on your team: a cross-border advisor, an immigration professional, and a cross-border accountant The healthcare gap, including Medicare Parts A and B, provincial waiting periods in Canada, and why the in-between period needs a strategy Resources The Great Return: Canadian’s Guide to Moving Home from the US, available on Amazon. Book page: letsmovetocanada.ca Canadians Heading South for the Winters: What You Don’t Know Will Hurt You, Gerry’s first book. Book page: snowbirdsheadingsouth.com Snowbirds US DayTracker, the travel app for tracking your days across the border: snowbirdsusdaytracker.com Snowbirds Expat Radio, the podcast, with more episodes featuring cross-border accountants, immigration lawyers, and advisors Mike’s podcast: [add link to host’s show]

What happens to your RRSP, your home, and your retirement savings the moment you follow your heart across the border?Of all the emails Gerry gets, the ones that worry him most come from snowbirds who have fallen in love with an American and are making a permanent move south with their hearts fully invested and their tax plans nowhere near ready. If you missed it the first time, this conversation with Calgary-based U.S. tax specialist Peter Blomfield of Blomfield Tax is the one to catch. Peter walks Gerry through the most common and costly mistakes Canadians make when going from snowbird to U.S. resident, from departure tax to state-level RRSP exposure, from LLC pitfalls to the principal residence trap.What You'll Learn Reporting requirements: Why the IRS's reporting rules catch most Canadians completely off guard, and what the penalties look like when you miss themTwo kinds of residency: The difference between immigration residency and tax residency, and why confusing the two can cost youState tax surprises: How state rules vary dramatically, and why Hawaii and California are two states where RRSP holders face a nasty surpriseCrystallizing RRSP gains: Why locking in gains inside your RRSP before you leave Canada may be one of the smartest moves you can makeThe principal residence trap: How the Canadian exemption differs from the U.S. version, and how a tax-free sale in Canada can become a taxable event the moment you cross the borderThe LLC warning: What every Canadian investor or entrepreneur needs to hear before setting up a U.S. business structureWho builds your structure: Why having a U.S. lawyer set up your investment structure without a cross-border accountant in the room is a recipe for penaltiesForeign tax credit: How rental income from a Canadian property gets reported once you are a U.S. residentA real-world scenario: Bruce and Susan have $2M in assets, an RRSP, cash, and a principal residence. What does departure planning actually look like?Resources and Links  Peter Blomfield, Blomfield Tax: blomfieldtax.comEmail Peter: [email protected] US Day Tracker app: https://snowbirdsusdaytracker.comGerry's book, Canadians Heading South for the Winters: What You Don't Know Will Hurt You: snowbirdsheadingsouth.com

Guest: Pat Fournier, JPS Accounting Services (Port Coquitlam, BC) You've decided to move back to Canada. You think the hard part is over. Gerry sits down with cross-border accountant Pat Fournier of JPS Accounting Services to walk through Chapter 2 of The Great Return, and the message is clear: leaving the US isn't something that just happens when you cross the border. It's something you have to prove, on paper, to two different tax authorities that don't talk to each other and won't figure it out for you. Pat has seen the mistakes up close, from Canadians who used a BC mailing address to open an investment account while still living full-time in the US, to returning residents who assumed their first year back gave them a free pass on foreign reporting. She and Gerry cover what actually triggers IRS and CRA recognition of a move, what happens to IRAs, 401(k)s, and Roth accounts when you cross the border, and why the T1135 form catches so many people off guard. What You'll Learn There's no punch card for leaving the US. The IRS doesn't automatically know you've gone. Green card holders who surrender their card need to file the appropriate form, and until it's filed, you're still considered a resident with ongoing filing obligations. CRA looks at the facts, not a date you pick. Car insurance, family location, a house purchase, where you're really living, all of it factors into when CRA decides your Canadian residency actually started. The Canadian address mistake. Using a Canadian mailing address to open an investment account while still living in the US can trigger CRA to treat you as a resident and tax your full worldwide income, long before you meant to make that move. The Roth IRA election most people miss. A Roth is tax-free in the US, but that status doesn't carry over automatically. Without filing an election letter with CRA in your first year back, Canada will tax the account's growth. Late elections are possible but not guaranteed. The IRA-to-RRSP "rollover" isn't really a rollover. Moving IRA or 401(k) funds into an RRSP means cashing out and facing US tax first. Pat explains why you need liquid cash on hand to cover the gap, and why some Canadian advisors push this move without fully weighing the cost. Social Security gets taxed differently than people expect. Once you're a Canadian resident, Canada taxes your US Social Security, not the IRS, per the treaty. Pat's advice: stop any voluntary US withholding before you move. The T1135 trap for returning Canadians. New immigrants to Canada get a one-year exemption from this foreign reporting form. Returning Canadians do not. It also covers more than the US equivalent (FBAR), including rental properties, and its reporting threshold is based on cost, not current value. RRSP contribution room doesn't show up on day one. Room is based on the prior year's Canadian earned income, so most people have zero room their first year back unless they're using carryforward room from before they left. Give yourself at least three months. Pat's rule of thumb for how much lead time to build into your planning before an actual move date. Resources & Links Guest: Pat Fournier, JPS Accounting Services, Port Coquitlam, BC Book: The Great Return: Canadians' Guide to Moving Home from the US — Chapter 2 sample now available on Amazon Snowbirds US Day Tracker letsmovetocanada.ca

Guest: Robert Clegg, CanadAmerican Tax Services Host: Gerry Scott Episode Overview A lot of Canadians who built a life in the United States assume that walking away from a green card is as simple as handing it back at the border. It is not. In this episode, Gerry sits down with cross-border tax specialist Robert Clegg of CanadAmerican Tax Services to unpack the U.S. Exit Tax, the rule that can turn a routine move back to Canada into a six-figure tax bill. Robert walks through how the IRS decides who counts as a covered expat, why the 8-out-of-15-year rule catches long-term green card holders off guard, and what really happens at the border when an officer decides your green card has been abandoned. Real client scenarios, including a near miss at the seven-year mark, illustrate just how much timing matters. Whether you are holding onto a green card out of habit, weighing citizenship, or planning your eventual return to Canada, this conversation lays out exactly what to check before you make a move. What You'll Learn What the U.S. Exit Tax actually is, and how it mirrors Canada's departure tax with a mark-to-market calculation on the day you renounce or abandon status The $2 million net worth threshold that determines whether you're a covered expat, and the roughly $800,000 exclusion available against any deemed gain Why deferred compensation, including 401(k)s and RRSPs, faces a 30 percent withholding if you're a covered expat, and why CPP, OAS, and Social Security are treated differently The 8-out-of-15-year rule for green card holders, including how even one day of residency in a given year counts toward the eight Why a green card does not simply expire after ten years for tax purposes, and the official abandonment process required to stop U.S. filing obligations How border officers assess whether you've abandoned your green card by living in Canada, and what filing a Canadian tax return as a resident signals What a reentry permit is and how it protects green card holders who plan to spend up to two years outside the U.S. without losing status Why there's no do-over once a green card is surrendered, and the limited exceptions for U.S. citizen spouses or children The case for taking U.S. citizenship before moving back to Canada if you ever want unrestricted reentry, including the Medicare timing consideration for retirees under 65 Practical consequences of renouncing, from B-2 visitor day limits to firearm import restrictions to how a Canadian DUI or criminal record can bar reentry for former citizens Resources & Links Guest: Robert Clegg, CanadAmerican Tax Services — cross-border personal, corporate, and partnership tax planning IRS Form 8854, Initial and Annual Expatriation Statement USCIS Form I-131, Application for Travel Document (includes the reentry permit for green card holders) USCIS naturalization eligibility tool snowbirdsheadingsouth.com This episode is for educational purposes only and does not constitute individualized tax, legal, or financial advice. Listeners should consult a qualified cross-border accountant, tax attorney, or financial advisor before making decisions about green card abandonment, U.S. citizenship, or a cross-border move.

Gerry sits down with Denise Hodgins, a REALTOR® with eXp Realty who specializes in lifestyle-driven moves to Vancouver Island. Together they dig into why Nanoose Bay, Parksville and Qualicum Beach have become such a draw for Canadians heading home and Americans relocating north, and they unpack two of the biggest financial landmines buyers need to understand before they fall in love with a listing: the foreign buyer ban and the speculation and vacancy tax. What They Discussed Denise's background and her focus on lifestyle-driven real estate moves across Vancouver Island Canada's foreign buyer ban, set to expire January 1, 2027, and why industry analysts don't expect lifting it to move affordability much Why Vancouver Island keeps winning people over: pace of life, beach access, year-round golf, and a housing market that still offers relative value The speculation and vacancy tax, which areas are currently exempt (Nanaimo, Lantzville, Parksville, Qualicum, Nanoose, French Creek, Errington, Coombs, Bowser, Deep Bay), and why exemption boundaries can be easy to misread What the tax actually costs: potentially $45,000+ annually for foreign owners, with different rates for Canadian citizens and permanent residents Why buyers need a full cross-border team in place before they fall in love with a house: REALTOR®, immigration lawyer, cross-border tax accountant, and cross-border financial advisor A cautionary story about a client who trusted a charming but unqualified advisor, and what it cost to clean up afterward FIRPTA withholding on the sale of US property, and why the IRS holds back a portion of proceeds until you prove you don't owe tax A tour of Nanoose Bay's Fairwinds community: golf course, wellness centre, marina, and the new Pheasant Glen clubhouse coming this fall Trails and biking in the area, plus planned expansions connecting Top Ridge Park to Coombs Links & Resources Connect with Denise: https://www.bcislandhomes.ca/ The Great Return: Canadian's Guide to Moving Home from the US — letsmovetocanada.ca Canadians Heading South for the Winters — snowbirdsheadingsouth.com Track your cross-border travel days — snowbirdsusdaytracker.com

Most people treat a Canadian-born grandparent as fun family trivia, not a legal pathway to citizenship. But thanks to a change in Canadian law, that old birth certificate could now be the key to citizenship, residency, and a new set of cross-border tax questions. That's the reality cross-border attorney Robert Clegg sees again and again, and it's what he unpacks in this episode. Robert returns from Victoria, BC to talk with Gerry about Canada's expanded "Lost Canadian" citizenship rules. Robert is a U.S. immigration and tax attorney based in Seattle and Victoria with 30+ years of cross-border experience. They dig into who qualifies, how to apply, and the realities of relocating to Vancouver Island. What You'll Learn: The Dec. 2025 rule change: citizenship now extends to grandchildren and great-grandchildren of Canadian-born ancestors.A real case study: how one American traced citizenship through his Alberta-born grandfather.Why 3-4 million Americans may be eligible, with 150,000+ applications filed and ~1 year wait times.Why dual citizenship is required before renouncing U.S. citizenship.How the BC Speculation and Vacancy Tax ties to citizenship status.Popular Vancouver Island landing spots: Victoria, Qualicum Beach, Cobble Hill, Nanaimo, Sydney.Why most renunciations happen after 5-50 years in Canada, not for political reasons.Why the ~$13M U.S. estate tax exclusion means most clients aren't exposed.The overlooked hurdle of rebuilding credit and banking across the border.

Guest Host: Laura Garfield | Co-Founder, Idea Decanter  |  Guest: Gerry Scott You spent years building a life in the US - a green card, a career, maybe even citizenship. So what happens to your taxes, your investments, and your retirement accounts the moment you decide to move back home to Canada? The tables are turned this episode: Laura Garfield, co-founder of Idea Decanter, steps in as host to interview Gerry Scott about his brand new book, The Great Return: Canadian's Guide to Moving Home from the US. It's the companion to Gerry's first book, Canadians Heading South for the Winters, and this time it's written for the reverse journey - Canadians coming home after years in the US, and Americans making the move north. Gerry and Laura get into why this move feels deceptively easy (same language, similar culture) when in reality it means untangling two completely different tax systems, the CRA and the IRS. They cover exit tax and the difference between a covered and non-covered expat, why cross-border financial advisors can't legally follow clients across the border, and why DIY moves so often lead to expensive mistakes. Laura also shares her own cross-Canada train trip, and Gerry brings up the Lost Canadians genealogy angle for Americans who may already qualify for Canadian citizenship. What You'll Learn Who The Great Return was written for, and why it applies to Americans moving to Canada too Why the CRA and IRS don't line up, even though crossing the border barely feels like leaving home The difference between a covered and non-covered expat, and why it matters for exit tax Why US states like California and Hawaii don't recognize the Canada-US tax treaty Why your US financial advisor can't legally advise you once you move to Canada What happens tax-wise to Roth contributions, employee stock purchase plans, and pensions after the move How the Lost Canadians genealogy path could mean Americans already qualify for citizenship Resources & Links The Great Return: Canadian's Guide to Moving Home from the US — letsmovetocanada.ca Canadians Heading South for the Winters — snowbirdsheadingsouth.com Snowbirds US DayTracker — snowbirdsusdaytracker.com

Nobody wants to think about what happens to their Florida condo or Arizona snowbird home after they're gone. But if you're a Canadian with US property and you haven't planned for it, your family could be facing an audit, a probate mess, and tax consequences that were entirely avoidable. That's the reality cross-border tax attorney Alexey Manasuev sees again and again in his practice, and it's exactly what he unpacks in this episode. Alexey returns to the show from Tampa Bay to talk with Gerry about cross-border estate and tax planning for Canadian snowbirds. Alexey is a US tax attorney admitted in New York and DC, and the founder of US Tax IQ, a boutique firm focused exclusively on US international tax planning, compliance, and structuring. Together, Gerry and Alexey dig into what really happens when a Canadian passes away owning US real estate without a plan in place, and how to make sure that doesn't happen to you. What You'll Learn in This Episode Why proactive planning matters: Alexey explains how problems with US property often surface only after death, when probate alerts the IRS to gaps left decades earlier, turning what should have been a non-issue into an audit. US estate tax exposure for Canadian-owned property: how a Florida, Arizona, or other US property can trigger US estate and gift tax obligations for a Canadian owner, even without US citizenship or residency. Domicile vs. residency: why US estate and gift tax exposure is based on the legal concept of domicile, a facts-and-circumstances test built around intent, not the same as ordinary tax residency. The LLC trap: why an LLC structure that a local US advisor recommends for domestic buyers can create serious problems for Canadian owners on both sides of the border. One will or two: when a single will can work for a cross-border estate, and why a US power of attorney for incapacity and medical decisions is often more important than a second will. The 2026 estate tax exemption threshold: how the $15 million federal base exclusion amount taking effect in 2026 factors into planning decisions. Sell now or hold for the next generation: the shifting trend Alexey is seeing, with some families selling US property as they age while others hold on for the lifestyle and pass it down. Why "campfire advice" is dangerous: why casual, well-meaning tips from friends, neighbors, or a local advisor unfamiliar with cross-border rules can create costly problems, and why a paid consultation with a qualified cross-border tax professional pays for itself. Resources and Links US Tax IQ Snowbirds US Day Tracker App Canadians Heading South for the Winters: What You Don't Know Will Hurt You, by Gerry Scott

If you have a Canadian ancestor somewhere in your family tree, you might not need to look very far back. A landmark change to Canadian citizenship law means that for millions of people, especially Americans, that ancestry could now open the door to a Canadian passport. And the person who can help you find that door is a genealogist. This week Gerry sits down with Sheila Hobeck, professional genealogist and founder of Kinalytic, based in Oakville, Ontario, to walk through what Bill C-3 actually means, how to document your Canadian lineage, and why DNA is rewriting family histories that paper records tried to keep buried. What You'll Learn in This Episode What Bill C-3 actually changes: effective December 2025, Canada eliminated the generational limit on citizenship by descent, meaning a Canadian ancestor anywhere in your history, if you can document it, may be enough to claim Canadian citizenshipWho counts as a lost Canadian and why historical acts stripped citizenship from individuals through marriage, birth abroad, and other circumstances that Bill C-3 now addressesHow to start the process through IRCC, when to bring in a Regulated Canadian Immigration Consultant, and when the situation calls for an immigration lawyerWhere genealogists search, from Ancestry and FamilySearch to physical archives and historical societies, and why not everything has been digitizedThe role of DNA in confirming lineage, identifying unknown relatives, and uncovering what Sheila calls NPEs, non-paternity events, where documents and biology don't matchHow AI is helping translate old records written in Quebec French, Latin, and paleographic script, and point researchers toward the right archivesWhy this matters beyond immigration, and what your ancestors' risks and journeys reveal once you start diggingResources and Links Sheila Hobeck, Kinalytic: kinalytic.comIRCC, Immigration, Refugees and Citizenship Canada: canada.ca/en/immigration-refugees-citizenshipFamilySearch (free): familysearch.orgAncestry: ancestry.caGEDmatch: gedmatch.comFamilyTreeDNA: familytreedna.comTrack your days across the border with DayTracker: snowbirdsusdaytracker.comCanadians Heading South - Buy the Book: snowbirdsheadingsouth.com

What Canadian Green Card Holders Need to Know Before They Surrender Status Guest: Robert Clegg, CanadAmerican Tax Services  |  Host: Gerry Scott Episode Overview A lot of Canadians who built a life in the United States assume that walking away from a green card is as simple as handing it back at the border. It is not. In this episode, Gerry sits down with cross-border tax specialist Robert Clegg of CanadAmerican Tax Services to unpack the U.S. Exit Tax, the rule that can turn a routine move back to Canada into a six-figure tax bill. Robert walks through how the IRS decides who counts as a covered expat, why the 8-out-of-15-year rule catches long-term green card holders off guard, and what really happens at the border when an officer decides your green card has been abandoned. Real client scenarios, including a near miss at the seven-year mark, illustrate just how much timing matters. Whether you are holding onto a green card out of habit, weighing citizenship, or planning your eventual return to Canada, this conversation lays out exactly what to check before you make a move. What You'll Learn What the U.S. Exit Tax actually is, and how it mirrors Canada's departure tax with a mark-to-market calculation on the day you renounce or abandon status The $2 million net worth threshold that determines whether you're a covered expat, and the roughly $800,000 exclusion available against any deemed gain Why deferred compensation, including 401(k)s and RRSPs, faces a 30 percent withholding if you're a covered expat, and why CPP, OAS, and Social Security are treated differently The 8-out-of-15-year rule for green card holders, including how even one day of residency in a given year counts toward the eight Why a green card does not simply expire after ten years for tax purposes, and the official abandonment process required to stop U.S. filing obligations How border officers assess whether you've abandoned your green card by living in Canada, and what filing a Canadian tax return as a resident signals What a reentry permit is and how it protects green card holders who plan to spend up to two years outside the U.S. without losing status Why there's no do-over once a green card is surrendered, and the limited exceptions for U.S. citizen spouses or children The case for taking U.S. citizenship before moving back to Canada if you ever want unrestricted reentry, including the Medicare timing consideration for retirees under 65 Practical consequences of renouncing, from B-2 visitor day limits to firearm import restrictions to how a Canadian DUI or criminal record can bar reentry for former citizens Resources & Links Guest: Robert Clegg, CanadAmerican Tax Services - cross-border personal, corporate, and partnership tax planning https://www.canadamericantax.com/meet-us.php IRS Form 8854, Initial and Annual Expatriation Statement: https://www.irs.gov/forms-pubs/about-form-8854 USCIS Form I-131, Application for Travel Document (includes the reentry permit for green card holders): https://www.uscis.gov/i-131 USCIS naturalization eligibility tool: https://www.uscis.gov/citizenship snowbirdsheadingsouth.com

If you bought a place in Arizona or Maui twenty years ago and never thought about what happens to it when you sell, or when you die, could it already be too late to avoid a tax shock you never saw coming? This week Gerry sits down with Robert M. Clegg, JD, LL.M, of CanadAmerican Tax Services, a dual Canadian and US cross-border tax specialist based on Vancouver Island, to walk through what really happens when a Canadian sells US real estate. From FIRPTA withholding and ITIN requirements to the currency trap and the long road of selling a property after an owner has died, this is the conversation to have before you let a realtor put the sign on the lawn. What You'll Learn in This Episode - Why your first call should be to a cross-border accountant, not the realtor, and how that single move takes the hidden tax shock off the table before the sign ever goes up - FIRPTA explained: how 10 to 15 percent of your gross sale price gets withheld up front, why California and Hawaii add their own layer on top, and why Arizona, Texas, and Nevada do not - Why each non-resident Canadian spouse must file a separate 1040NR with their own ITIN, and how escrow companies routinely get this wrong by issuing one withholding slip under a single number - The currency trap: how a weak Canadian dollar can turn a 700,000 US gain into a far bigger Canadian one, and why you need the exchange rate at purchase, at sale, and at every renovation - How the foreign tax credit stops you from being taxed twice, why only half your gain is taxable in Canada, and roughly what is left to pay the CRA once the US tax is credited - Why the 1031 like-kind exchange your realtor keeps recommending simply does not work for Canadians - What changes when parents pass away still owning the property, from the US estate return on assets over 60,000 to a clearance certificate that can take two to three years before you can sell Resources & Links Robert M. Clegg, JD, LL.M, CanadAmerican Tax Services: canadamericantax.com FIRPTA Canada, Calgary-based FIRPTA specialists: firptacanada.com Track your days across the border with DayTracker: snowbirdsusdaytracker.com Canadians Heading South - Buy the Book: https://a.co/d/01Ryf45Z Note: the forms, thresholds, and rates discussed are general and reflect the conversation as recorded. Confirm your own situation with a cross-border tax professional and your Canadian accountant before selling.

If you bought a place in Palm Springs or Maui twenty years ago and never thought about what happens when you sell it — or when you die — is it too late to fix that? In this episode, Gerry sits down with Kevin Kirkpatrick of Bordera Tax and Immigration Law — a dual Canadian-US lawyer based in Seattle, with his main office in Calgary — to walk through the estate planning issues that catch Canadians off guard on both sides of the border. From US estate tax thresholds to the 8-of-15 green card rule to FIRPTA withholding on US property sales, this is the conversation to have before you assume your Canadian will is enough. What You’ll Learn in This Episode Why the $60,000 US asset threshold matters — and what counts as “US stuff” when the CRA is done with you How the Canada-US Tax Treaty provides Canadian residents a pro-rated US estate tax credit, and why the current high exemption benefits most Canadians What happens when a US citizen inherits a Canadian private corporation — and why controlled foreign corporation rules create reporting obligations even for family businesses The 8-of-15 rule for green card holders: when you become a long-term resident subject to US exit tax, and a treaty exception that may reduce your exposure Why dual-licensed doesn’t mean one lawyer handles everything — and how Kevin and his partner Asim structure their practice across US and Canadian tax law FIRPTA explained: how 15% gross withholding on US property sales works, why California and Hawaii add their own layer, and what your options are Whether trusts, non-recourse mortgages, or life insurance can still help if you bought your US property decades ago without any planningResources & Links Kevin Kirkpatrick — Bordera Tax and Immigration Law: bordera.ca FIRPTA Canada (Calgary-based FIRPTA specialists): firptacanada.com Track your days across the border: snowbirdsusdaytracker.com Canadians Heading South - Buy the Book: https://a.co/d/01Ryf45Z

Guest Host: Laura Garfield | Co-Founder, Idea Decanter You’ve been heading south for years and doing everything the same way. So why does it feel like the rules keep changing? This episode is a little different. Gerry’s producer Laura Garfield flips the script and puts Gerry in the hot seat to celebrate the launch of his brand new book: Canadians Heading South for the Winters — What You Don’t Know Will Hurt You. After eight years of fielding the same snowbird questions week after week, Gerry sat down and wrote the guide he’d always wished existed. This episode is the story behind that book — what it covers, why he wrote it, and why he believes no snowbird should be without it. What You’ll Learn Why immigration and tax are two completely separate conversations — and why mixing them up is one of the most common and costly snowbird mistakes What “I’ve always done it this way” actually means at the border — and why it’s no longer a safe assumption How border agents use discretion, and why your travel pattern matters more than your intentions What happens when you’re denied entry — and why you can’t just drive to the next crossing and try again Why the book is designed as a reference guide, not a cover-to-cover read The growing trend of snowbirds selling their U.S. properties — and why it’s a taxable cross-border event most people aren’t prepared for Why Gerry split what started as one book into two — and what the second book, The Great Canadian Return, will cover Where to get your copy: http://snowbirdsheadingsouth.com/ About the Book Canadians Heading South for the Winters — What You Don’t Know Will Hurt You Gerry Scott’s debut book is a practical reference guide covering the 10 most important topics every Canadian snowbird needs to understand before heading south — immigration, tax, healthcare, residency rules, day tracking, border crossings, and more. At 180+ pages, it’s built to sit beside you, not just be read once. Available now at www.snowbirdsheadingsouth.com. Resources Get the book: http://snowbirdsheadingsouth.com/ Track your days: snowbirdsusdaytracker.com

What really happens to your money, your investments, and your tax obligations the moment you leave Canada for the United States? Gerry sits down with Kevin Heath of GTA Accounting to walk through what actually happens when Canadians exit Canada and become U.S. tax residents. From departure tax and deemed disposition to TFSA traps and state-level surprises, this is the conversation to have before your move becomes official on paper. • Why departure tax is triggered when you leave Canada and how deemed disposition forces you to report gains even if you have not sold anything• Which assets are included in departure tax calculations and why Canadian real estate and registered accounts are treated differently• How deferring departure tax works and when the CRA may require security before approving it• Why TFSAs lose their tax-free status in the U.S. and how mutual funds and ETFs inside them can create complex and costly reporting requirements• What PFIC rules are and why holding Canadian funds in the U.S. can trigger higher tax rates and steep penalties• How owning a Canadian corporation creates U.S. reporting obligations under Form 5471 and the penalties tied to getting it wrong• Why RRSPs are treated differently at the federal and state level and how states like California and Hawaii can tax growth inside the account• When it makes sense to liquidate investments before moving and start fresh in the U.S. with cash• How timing your move can impact whether your income or withdrawals are taxed in Canada, the U.S., or both• Why more Canadians are choosing to work in the U.S., from lower tax rates to currency advantages and broader career opportunities Resources and Links:GTA Accounting Snowbird US Day Tracker App: Available on the App Store and Google Play Coming Soon: The Snowbirds Expat Radio Book

Of all the conversations Gerry has about cross-border life, the ones involving Canadians who have quietly become US tax residents without realizing it are among the most urgent.  In this episode, Gerry sits down with Karlene Mulraine of Brij Professional Corporation to walk through what Canadian digital nomads actually need to understand about working in the United States. From the rolling three-year calculation that catches even financially savvy Canadians off guard, to the sticky-state problem that can make double taxation impossible to avoid, to the very real cost of trying to file a cross-border return on your own, this is the conversation to have before your wanderlust makes the decision for you. Why the 183-day rule is not the tax shield most Canadians believe it to be, and how the Substantial Presence Test actually works across three calendar years How Form 8840, the Closer Connection Exception Statement, can protect your Canadian tax status even after you have technically triggered US residency Why Canadian employers are almost never equipped to handle US payroll sourcing, and what that means for the employee working from Palm Springs What happens when you file both a 1040NR and a T1, and why the CRA's foreign tax credit review process is where most DIY cross-border returns fall apart Why New York, California, and Hawaii are sticky states, and why working in any of them may leave you exposed to true double taxation that no treaty can fix How treaty tiebreaker positions under Article 4 of the Canada-US Tax Treaty can be used as a planning tool, not just a last resort What a CRA reassessment looks like in practice when a $30,000 foreign tax credit claim gets reversed, and the interest and penalties that follow Why tracking your days across jurisdictions is the single most foundational habit any cross-border traveler or worker can build What You'll Learn in This EpisodeResources and Links Karlene Mulraine - Brij Professional Corporation: https://brij.tax/ Snowbird US Day Tracker App: Available on the App Store and Google Play Coming Soon: The Snowbirds Expat Radio Book