Guides

Straight answers, written by the people who’d file it.

1,423 plain-English guides on cross-border moves, US and Canadian returns, and small-business money. Each one ends in what to do next, and says when a written Position Check is the smarter first step.

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CROSS-BORDER A Canadian Corporation With a U.S. Shareholder

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1,423 guides

Cross-Border Tax (U.S.–Canada)

Cross-Border Mortgages: Who Will Lend, What the Interest Deducts Against, and the Structures That Waste or Save the Write-Off

September 15, 2026

Financing property across the border is two problems: getting the loan (thin credit files, cross-border lenders, the currency question) and taxing the interest (the US deducts home mortgage interest; Canada doesn't — but both deduct interest against rental income, and the tracing rules decide everything). Here is the lending landscape and the deductibility map.

Cross-Border Tax (U.S.–Canada)

Cross-Border REIT Investing: US REITs in Canadian Hands, Canadian REITs in American Hands, and the Account-Location Rules That Decide the Yield

September 15, 2026

Real estate exposure through REITs swaps property-level tax problems for securities-level ones: US REIT distributions carry their own withholding quirks (return of capital, capital gain distributions, and rates that differ from ordinary dividends), Canadian REITs are presumptively PFICs for US persons, and the RRSP/TFSA/taxable location decision moves after-tax yield by whole percentage points. Here is the map.

Cross-Border Tax (U.S.–Canada)

Does a 1031 Exchange Work for Canadian Property? The Foreign-for-Foreign Rule, Canada's Missing Rollover, and What Cross-Border Investors Use Instead

September 15, 2026

US investors defer real estate gains through 1031 exchanges — but US property is not like-kind to foreign property, so you can't exchange Phoenix for Toronto. Foreign-for-foreign works on the US side; Canada, meanwhile, has no 1031 at all and taxes the disposition regardless. Here is what survives the border, what doesn't, and the substitute strategies.

Cross-Border Tax (U.S.–Canada)

The Family Cottage With Cross-Border Heirs: Deemed Dispositions, American Children, and the Succession Structures That Actually Keep the Place

September 15, 2026

Passing the cottage down is Canada's classic estate problem — the deemed disposition at death taxes decades of appreciation with no cash to pay it — and American heirs add a second layer: rental characterization, 3520 reporting, and eventually their own US-situs planning in reverse. Here is the succession toolkit with the cross-border overlay.

Cross-Border Tax (U.S.–Canada)

A FATCA Letter From Your Canadian Bank: What It Means, What They Already Report, and the Right Order of Next Moves

September 15, 2026

The letter asking about your US status — a W-9 request, a 'US indicia' questionnaire — means your bank's systems flagged you, and under the Canada-US information-sharing agreement your account data may flow to the IRS through the CRA. The letter itself is routine; the compliance status it illuminates is the real question. Here is what to do, in order.

Cross-Border Tax (U.S.–Canada)

Florida Property Tax for Canadian Owners: No Homestead, No Cap, and the Assessment Math Snowbirds Should Run Before Buying

September 15, 2026

Florida's celebrated property tax breaks — the homestead exemption and the Save Our Homes cap — belong exclusively to permanent Florida residents, which excludes every snowbird by definition. Canadian owners pay full millage on full assessed value with a softer 10% cap, and the gap versus their homesteaded neighbors widens every year. Here is the system, the math, and what actually helps.

Cross-Border Tax (U.S.–Canada)

Holding US Real Estate Through a Canadian Corporation: the Structure That Solved a 1990s Problem and Creates Five Modern Ones

September 15, 2026

The Canadian holdco owning the Florida house was once standard estate-tax planning; today it manufactures shareholder benefits on every personal-use week, corporate FIRPTA and branch tax on exit, stacked filings in both countries, and worse rates on rental income — while the treaty credits solved the original problem for most estates. Here is why the structure persists, what it actually costs, and how existing ones unwind.

Cross-Border Tax (U.S.–Canada)

How Americans Should Hold Canadian Real Estate: Personal Title Wins, the LLC Fails Twice, and the Narrow Cases for Anything Else

September 15, 2026

The American buying Canadian property inherits the mirror of every Canadian-buying-US structuring question — and the answer mirrors too: personal title beats the vehicles. The US LLC that protects at home misclassifies in Canada; trusts import two countries' reporting; corporations stack taxes. Here is the holding-structure decision from the American side, case by case.

Cross-Border Tax (U.S.–Canada)

How Far Back Can the CRA and IRS Go? Reassessment Periods, the Six-Year Doors, and the Years That Never Close

September 15, 2026

Each system promises finality on a clock: Canada's normal reassessment period runs three years from assessment, the IRS's statute runs three from filing — and each has doors that extend to six, and conditions that suspend the clock entirely. Unfiled returns and unreported foreign assets are the classic forever-cases. Here is the limitation map for cross-border filers.

Cross-Border Tax (U.S.–Canada)

An IRS Audit While Living in Canada: What Expat Audits Actually Look Like and How to Run One From Abroad

September 15, 2026

For a US citizen in Canada, an IRS audit almost never means a visit — it means correspondence: a letter proposing questions or changes, deadlines that assume US mail speeds, and issues that cluster around the expat forms. Here is what triggers expat audits, how the process runs remotely, and the file management that decides outcomes.

Cross-Border Tax (U.S.–Canada)

The IRS CP2000 Notice With Canadian Income in the Mix: Why the Matching Computer Is Wrong More Often for Expats, and How to Answer It

September 15, 2026

A CP2000 proposes extra tax because the IRS's information returns don't match your 1040 — and for cross-border filers the mismatch is often the computer missing your foreign tax credit, double-counting a slip, or reading gross where you correctly reported net. It is a proposal, not a bill. Here is how to read one, and the response that closes it.

Cross-Border Tax (U.S.–Canada)

IRS Penalty Relief: First-Time Abatement's Free Pass, the Reasonable Cause Standard, and How Cross-Border Filers Should Ask

September 15, 2026

The IRS waives billions in penalties annually through two doors: First Time Abate — a clean-history administrative pass for filing and payment penalties, granted almost mechanically — and reasonable cause, the facts-and-circumstances standard that covers what FTA doesn't, including the international information return penalties expats fear most. Here is how each works and how to write requests that succeed.

Cross-Border Tax (U.S.–Canada)

Land Transfer Taxes and Closing Costs: What It Actually Costs to Buy in Canada vs the US, Line by Line

September 15, 2026

Canadian buyers pay land transfer taxes that can reach 4-5% in Toronto with the foreign-buyer surtaxes on top; US buyers trade lower transfer taxes for title insurance, higher legal-adjacent fees, and property-tax proration quirks. Neither side's costs are deductible for personal homes — but every line lands somewhere: basis, expense, or nowhere. Here is the closing statement decoded, both directions.

Cross-Border Tax (U.S.–Canada)

Owing the CRA While Living in the US: Payment Arrangements, What Canadian Collections Can Reach, and the Citizen Carve-Out Running the Other Way

September 15, 2026

A CRA debt follows the emigrant south — interest compounds, Canadian-source income and accounts remain exposed, benefits and refunds offset, and the treaty lets the CRA ask the IRS to collect finally-determined debts, except generally against US citizens whose debt arose while they were US citizens. Here is the southbound debtor's map, and the arrangements that resolve it.

Cross-Border Tax (U.S.–Canada)

Owing the IRS While Living in Canada: Payment Plans, the Offer Route, and What US Collections Can Actually Reach

September 15, 2026

A US tax debt doesn't expire at the border — interest and penalties run, refunds offset, passports certify, and the treaty gives the IRS a collection arm in Canada in some cases. But the resolution menu also works from abroad: installment agreements, currently-not-collectible status, and offers in compromise. Here is the debtor's map from north of the border.

Cross-Border Tax (U.S.–Canada)

Pre-Construction Condos Across the Border: Assignment Sales, the New Housing Rebate, and Why the Flipping Rules Watch This Market

September 15, 2026

Pre-construction buying runs on its own tax rails: deposits and occupancy fees before title, GST/HST embedded in new-home prices with rebates that depend on your intentions, assignment sales taxed as business income with GST on top, and the flipping rule timing everything. Add a border — the US buyer of a Toronto pre-con, the Canadian buying Miami pre-construction — and intentions get audited. Here is the map.

Cross-Border Tax (U.S.–Canada)

Canada's Principal Residence Exemption vs America's Section 121 Exclusion: Two Home-Sale Shelters That Don't Match, and How Movers Coordinate Them

September 15, 2026

Canada exempts the designated principal residence's gain without dollar limit; the US excludes up to $250,000/$500,000 with ownership-and-use tests. For anyone who files in both systems — or moves between them — the mismatches decide real tax: unlimited vs capped, designation vs mechanical tests, and the timing windows that reward planned sales. Here is the side-by-side and the coordination playbook.

Cross-Border Tax (U.S.–Canada)

Property Flipping Rules in Canada and the US: the 365-Day Deemed Business Income Rule, the Dealer Doctrine, and Where Cross-Border Flippers Get Taxed Twice at Full Rates

September 15, 2026

Canada now deems profit on housing sold within 365 days to be fully-taxed business income — no capital treatment, no principal residence exemption — while the US reaches the same result through its dealer-versus-investor doctrine and holds short gains at ordinary rates anyway. Flip across the border and both systems' full-rate regimes meet the same profit. Here is the map, the exceptions, and the intention evidence that decides the close cases.

Cross-Border Tax (U.S.–Canada)

The Underused Housing Tax: Who Had to File for 2022–2024 — and Why It's Now Eliminated

September 15, 2026

Canada's UHT was a 1% annual tax on underused residential property aimed at foreign owners — and Budget 2025 eliminated it for 2025 and later years. But the 2022, 2023, and 2024 returns still stand, and their real teeth were always the filing rules: affected owners filed a return per property even when fully exempt, with penalties attached to the missing form. Here is the owner-by-owner sort, the exemption map, and what the elimination does and does not erase.

Cross-Border Tax (U.S.–Canada)

Unfiled Canadian Returns as a US Resident: Arbitrary Assessments, the VDP Route, and Catching Up From South of the Border

September 15, 2026

Behind on Canadian filings while living in the US — the emigrant who never filed the departure year, the non-resident landlord without 216 returns, the American with abandoned Canadian years? The CRA's toolkit includes assessments it writes for you; yours includes the VDP, late elections, and real numbers that beat arbitrary ones. Here is the northbound catch-up.

Cross-Border Tax (U.S.–Canada)

Unfiled US Returns as a Canadian Resident: How Many Years Back, Which Procedure, and What the Catch-Up Actually Costs

September 15, 2026

The American in Canada with years of unfiled 1040s faces a question with real procedural answers: streamlined's three-plus-six for the eligible, six years as the general practice for delinquent filers, and every year technically open because unfiled statutes never start. The tax usually rounds to little; the choice of route is everything. Here is the decision tree.

Cross-Border Tax (U.S.–Canada)

Passport Revocation for Tax Debt: How the IRS Certification Works, the Thresholds and Exceptions, and Getting Uncertified From Canada

September 15, 2026

Owe the IRS enough — an inflation-adjusted threshold ($66,000 for 2026) — with a lien filed or levy issued, and the IRS certifies the debt to the State Department, which can deny renewals and revoke passports. For an American in Canada whose passport is a practical necessity, this is the collection pressure that bites. Here is the machinery, the exits, and the timeline.

Cross-Border Tax (U.S.–Canada)

What Happens to My 401(k) When I Move to Canada? Leave It, Roll It, or Move It — the Three Options Priced

September 14, 2026

A 401(k) survives the move to Canada intact: the treaty defers Canadian tax on its growth, and distributions are taxed where you live when you take them. The real questions are whether to roll it to an IRA, whether an RRSP transfer ever makes sense, and how withdrawals will be taxed on both sides in retirement. Here are the three options with the tax mechanics of each.

Cross-Border Tax (U.S.–Canada)

529 Plans When the Family Moves to Canada: Still Tax-Free to the IRS, Just Another Account to the CRA

September 14, 2026

A 529 plan keeps every US advantage after a move to Canada — tax-free growth, tax-free qualified withdrawals, even for many Canadian universities. What it loses is Canadian recognition: the CRA has no category for it, and the prudent treatment taxes its growth annually on the Canadian return. Here is how families handle the gap, and when to spend, hold, or wind down.

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