2,121 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.
Page 81 of 89, newest first.
The entity choice changes how much self-employment tax an owner-operator pays and how much liability protection exists. Compare LLC, S-Corp, and sole.
US TaxIf you own or operate a truck with a taxable gross weight of 55,000 pounds or more, the IRS wants a Form 2290 from you every year.
US TaxOwner-operators pay federal excise tax on every gallon of diesel. On top of that, every state levies its own fuel tax, and the rates vary wildly.
US TaxOwner-operators are high-audit-risk taxpayers. Large deductions, cash operations, and per diem claims put truckers on the IRS radar.
US TaxHow the IRS decides whether your truck lease is a true lease or a conditional sale, and why that controls whether you deduct the payments or depreciation and interest.
US TaxThe full list of owner-operator tax deductions, how per diem works, when actual expenses beat the standard mileage rate, and what records the IRS expects.
US TaxHow taxes work for W-2 company drivers versus 1099 owner-operators, what each side can deduct, and what changes when you switch from one.
US TaxSelf-employed truckers can shelter $60,000 or more per year from tax with the right retirement plan. Most owner-operators are good at making money.
US TaxEach mechanism has different dollar limits, different income limitations, and different consequences when you eventually sell or trade the truck.
US TaxWhen a business withholds federal income tax, Social Security, and Medicare from employees' paychecks but does not send those withheld amounts to the IRS.
US TaxWhen you bill the federal government for costs incurred on a contract, the government does not pay for everything. Covers key rules, filing requirements,.
Cross-BorderUS real property is a US-situs asset for estate tax purposes, and the $60,000 NRA exemption covers almost nothing. Covers treaty provisions, foreign tax.
Cross-BorderListing a US LLC on Airbnb changes the trade-or-business classification, withholding, and FAPI on the Canadian side. Compare LLC, S-Corp, and sole.
Cross-BorderA US citizen or green card holder as trustee can change a Canadian trust's US classification, trigger annual reporting. Covers treaty provisions, foreign.
Cross-BorderHow the US wash sale rule and Canada's superficial loss rule interact for cross-border investors harvesting tax losses across both countries.
Canadian TaxThe CRA sends review letters, processing reviews, and full audits. Most people call all of them an audit, but the response strategy changes with each type.
Canadian TaxWhat happens when the CRA starts collecting: Requirements to Pay, wage garnishment, frozen accounts, liens, and the five ways to stop or slow it.
Canadian TaxWhat the CRA's gross negligence penalty under section 163(2) requires, how it differs from a regular penalty, and the burden of proof the CRA must meet.
Canadian TaxHow to file a CRA notice of objection, the 90-day deadline, what to write, real success rates, and your options if the CRA says no. Includes Form T400A.
Canadian TaxWhat to do when you disagree with a CRA reassessment. Objection deadlines, what to write, real success rates, interest during the dispute, and Tax Court.
Cross-BorderThe T1135 late filing penalty is $25 a day up to $2,500 per form, even with no tax owing. Gross negligence adds more. Here's how relief and the 2025 VDP rules work.
Cross-BorderIf you are a US person with Canadian filing obligations (or a Canadian resident with US filing obligations) and you are behind on both sides.
Cross-BorderFBAR penalties run up to $16,536 per report non-willful and the greater of $165,353 or 50% per account willful. How the IRS sets the amount, and which route fits your facts.
Cross-BorderThe IRS now considers reasonable cause statements on late Forms 3520 and 3520-A before assessing a penalty. What that means for TFSA, RESP and gift penalties, and abatement.