Guides

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

1,407 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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1,407 guides

Cross-Border Tax (U.S.–Canada)

My US LLC Is Now on Airbnb. What Changed for Canadian Tax? Everything, Because Canada Thinks the LLC Is a Corporation

September 7, 2026

A Canadian who put a US rental into an LLC and lists it on Airbnb has a US disregarded entity earning rent and a Canadian foreign affiliate earning FAPI. Here is what the LLC does to the Canadian return, the Form 5472 the US now requires, the platform's W-9 and 1099-K, and how to unwind it.

Cross-Border Tax (U.S.–Canada)

A Canadian Starting a US Business: Entity Choice, the LLC Trap, and the Filings on Both Sides

September 6, 2026

Entity choice, state registration, the EIN, US tax filing, Canadian reporting, and the treaty and visa intersections for a Canadian launching or buying a US business. Start with the entity, because the wrong one costs double tax.

CFO

Dental Practice Entity Structure: LLC, S-Corp, Partnership, and When to Change

September 3, 2026

How Florida dentists should think about PLLCs, professional associations, S-corp elections, and partnerships — the self-employment tax math, the QBI wrinkle, and the triggers for changing.

CFO

LLC or S-Corp for Your Restaurant? The Payroll-Tax Math and the Right Time to Switch

September 3, 2026

Nearly every restaurant should be an LLC for liability. The real question is when to elect S-corp taxation — the self-employment tax math, the reasonable-salary rules, and the traps for multi-owner and multi-location groups.

Cross-Border Tax (U.S.–Canada)

Canadian on an E-2 Investor Visa: The Tax Setup That Makes or Breaks Your U.S. Business

July 3, 2026

The E-2 lets Canadians buy or build a U.S. business — and the tax structure you choose on day one follows you for years. Entity choice (and the LLC trap), your dual-status arrival year, Canada's departure tax on a business owner, and the reporting your Canadian accounts trigger.

Cross-Border Tax (U.S.–Canada)

U.S. LLCs for Latin American Entrepreneurs: What You Actually Owe the IRS

June 22, 2026

A U.S. LLC owned from Latin America isn't automatically tax-free — and Form 5472 carries a $25,000 penalty for getting it wrong. What you actually owe the IRS, and why your entity and your personal U.S. residency are two separate questions.

Cross-Border Tax (U.S.–Canada)

Should a Canadian Own a U.S. LLC? Usually Not — Here's Why

June 15, 2026

The LLC is America's favorite business structure — which is exactly why so many Canadians get talked into one. For a Canadian owner, an LLC can create double taxation the U.S. and Canada were supposed to prevent. Here's the trap.

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