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Guides

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

971 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 Diagnostic is the smarter first step.

All Cross-BorderUS TaxCanadian TaxSmall Business & BookkeepingCFO & AdvisoryTax Planning

Page 32 of 41, newest first.

Cross-Border

RRSP and RRIF on death: what a US-person beneficiary needs to know

A Canadian RRSP or RRIF that was tax-deferred for decades becomes fully taxable when the holder dies.

Aug 27, 2026
US Tax

Schedule E vs Schedule C for Rentals: When Short Stays Trigger Self-Employment Tax

Traditional rentals go on Schedule E. The default for rental real estate income is Schedule E, where it is not subject to self-employment tax.

Aug 27, 2026
Cross-Border

SDOP vs SFOP: Which Streamlined Track Do I Qualify For?

SDOP and SFOP are one streamlined program with two tracks. Miss the non-residency call and a $500,000 balance costs $25,000 instead of zero.

Aug 27, 2026
US Tax

Self-Directed IRA Real Estate: The UBIT and UDFI Tax Most CPAs Miss

A self-directed IRA can buy real estate, but if the IRA uses a mortgage (non-recourse debt) to fund the purchase.

Aug 27, 2026
Cross-Border

Selling a Cross-Border STR: The Exit Checklist

Selling a US vacation rental as a Canadian resident triggers filings on both sides of the border, and the sequencing matters.

Aug 27, 2026
Cross-Border

Canadian Snowbird Renting on Airbnb: The Full Tax Picture

The complete tax picture when a Canadian snowbird rents a Florida condo on Airbnb part of the year: US reporting, the 871(d) election, IRC 280A.

Aug 27, 2026
Cross-Border

Spousal trusts in Canada: cross-border planning for mixed-status couples

A Canadian spousal trust lets you transfer property to a trust for your spouse's benefit without triggering an immediate tax bill.

Aug 27, 2026
US Tax

The Short-Term Rental Loophole: Can STR Losses Offset My W-2 Income?

A short-term rental with an average stay of 7 days or less is not a rental activity for passive loss rules.

Aug 27, 2026
Cross-Border

What Happens to Your RRSP, TFSA, and RESP in Streamlined Filing

An RRSP gets treaty deferral and light reporting. A TFSA gets none of that: it's a foreign trust, taxed every year, on Forms 3520 and 3520-A.

Aug 27, 2026
Cross-Border

Streamlined Filing for Americans Abroad (Non-Canada)

If your bank in London, Frankfurt, Tel Aviv, Dubai, Singapore, or Sydney sent you a letter asking for a US tax identification number you don't have.

Aug 27, 2026
Cross-Border

What Happens After a Streamlined Filing? Audit Risk and What to Expect

After you submit streamlined returns and FBARs, here's what the IRS actually does with them, the real audit risk, and what you owe going forward.

Aug 27, 2026
Cross-Border

Streamlined Filing for Canadian Snowbirds Who Became US Tax Residents

A snowbird who crossed the substantial presence threshold may owe no US tax but face steep FBAR and Form 8938 penalties. Streamlined filing closes the gap.

Aug 27, 2026
Cross-Border

Why Streamlined Submissions Get Rejected (and How to Avoid It)

Streamlined filing isn't a rubber stamp. The IRS rejects incomplete packages, wrong track selections, and weak non-willfulness certifications.

Aug 27, 2026
Cross-Border

How Cryptocurrency Complicates a Streamlined Filing Catch-Up

A streamlined catch-up is already a reconstruction project: three years of returns, six years of FBARs, one non-willfulness statement.

Aug 27, 2026
Cross-Border

Streamlined Filing for Married Couples: Joint Filers and Both-Spouse Rules

Most IRS streamlined guidance reads as if you're a single filer. You have unreported accounts, you file the package, and you're done.

Aug 27, 2026
Cross-Border

How Does Streamlined Filing Work for Retirees with Canadian Pensions?

Retirees collecting CPP, OAS, RRIF, or private pensions in Canada can catch up through SFOP with zero penalty.

Aug 27, 2026
Cross-Border

Streamlined Filing for Self-Employed and Business Owners

Self-employment makes streamlined filing harder and costlier: Schedule C, SE tax in arrears, estimated tax penalties that survive, Form 5471, QBI.

Aug 27, 2026
Cross-Border

State Tax After Streamlined Filing: What the IRS Program Doesn't Cover

You filed the streamlined package. Three years of federal returns, six years of FBARs, the certification, maybe the 5% penalty check.

Aug 27, 2026
Cross-Border

What Is the Streamlined Foreign Offshore Procedure, and Do I Actually Qualify?

SFOP clears five IRS penalty categories for qualifying non-willful citizens and green card holders abroad.

Aug 27, 2026
Cross-Border

I Have a Green Card and Live in Canada. Can I Use Streamlined to Catch Up on US Taxes?

Usually yes, but the green card raises a second question streamlined alone doesn't answer: are you still a US tax resident, and do you want to be?

Aug 27, 2026
Cross-Border

How do I write a non-willfulness certification the IRS will actually accept?

The non-willfulness certification, Form 14653 if you live outside the United States, Form 14654 if you live inside it.

Aug 27, 2026
Cross-Border

Streamlined vs. Voluntary Disclosure: When Willfulness Changes the Calculus

The IRS Streamlined Filing Compliance Procedures are the most commonly recommended path for US persons who are behind on their offshore reporting.

Aug 27, 2026
Cross-Border

Streamlined Filing With PFICs: Canadian Mutual Funds

Canadian mutual funds are PFICs, RRSP and TFSA holdings included, and each needs its own Form 8621 every covered year.

Aug 27, 2026
Cross-Border

Testamentary trusts after 2016: GRE and QDT rules in Canada

A testamentary trust is any trust that arises on (and because of) a person's death, typically created by a will.

Aug 27, 2026