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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

Small Business Tax

Gym and Fitness Studio Deductions: The Equipment, the Build-Out, the Memberships Paid in Advance, and the Instructors Who Teach Elsewhere Too

September 30, 2026

A gym or boutique fitness studio is a lease, a build-out, and a floor of equipment, paid for by memberships billed monthly or annually in advance — with a January that sells a year of memberships in a month, instructors whose classification is the sector's hardest question, and a retail and supplement line that carries sales tax. Here is each deduction, the membership timing, the classification test for class instructors, and the specified-service exclusion fitness enjoys.

Small Business Tax

Gym and Fitness Studio Entity and Estimated Taxes: The Opening-Year Loss, the S Election That Waits, and the January That Sells the Year

September 30, 2026

A gym's entity decision is shaped by its opening year — a build-out and equipment expensed into a loss that an S corporation owner can't use without basis — and its estimated taxes are shaped by January, when the resolution season sells a year of memberships in a month. Here is both, for a single boutique studio, a full-size gym, and a franchise location.

Small Business Tax

Home Care Agency Entity and Estimated Taxes: The S Election, the Skilled Line That Changes the Classification, and the Medicaid Receivables

September 30, 2026

A home care agency's entity decision is standard S election arithmetic on an administrator's salary — with a payroll that always exists — plus one structural choice: whether a skilled home health line (nursing and therapy) belongs in the same entity as the non-medical care, because the skilled line is a specified service trade and the non-medical line isn't. The estimated taxes run on a payer mix whose Medicaid share arrives months late. Here is both.

Small Business Tax

Home Care Agency Taxes: Caregiver Overtime, Travel Time Between Clients, the Medicaid Waiver Lag, and the Companionship Exemption You Can't Use

September 30, 2026

A non-medical home care agency is a payroll business: caregivers are most of the cost, the Department of Labor has taken away the companionship exemption for third-party employers, travel time between clients is compensable, and the revenue arrives from private pay, long-term care insurance, and Medicaid waiver programs that pay weeks late. Here is the payroll and classification analysis, each deduction, the payer-mix timing, and the registry model that tries to avoid being the employer.

Small Business Tax

Hotel and Motel Taxes: Occupancy Taxes, the Franchise Flag, the PIP Renovation, and the Cost Segregation That Makes the First Year

September 30, 2026

A hotel is real estate operated as a business — nonresidential property depreciated over thirty-nine years unless a cost segregation study moves the furniture, fixtures, and site work into short lives — with a franchise flag whose fees and required renovations shape the return, occupancy taxes collected for several governments, and a staff whose tips and housekeeping payroll follow the hospitality rules. Here is each piece, and why a hotel is a trade or business rather than a passive rental.

Small Business Tax

Hotel Ownership Entity Structure: The Property LLC, the Operating Company, the Management Agreement, and the Investor Who Is Passive

September 30, 2026

Hotels are usually owned by investor groups — a partnership-taxed LLC with a sponsor and passive investors — and the structure has to answer questions a single-owner business doesn't: who operates the hotel, whose losses are passive, how the sponsor is paid, and whether the property and the operations belong in separate entities. Here is the analysis for an owner-operator, a syndicated hotel with passive investors, and a family that owns several properties, plus the estimated taxes a hotel's season and first-year loss produce.

Small Business Tax

Independent Pharmacy Entity and Succession: The Owner-Pharmacist, the S Election, the LIFO Reserve, and the Buyer Who Wants the Prescription Files

September 30, 2026

An independent pharmacy's entity decision runs on the owner-pharmacist's market salary, a specified-service label that zeroes the QBI deduction above the range, and a board of pharmacy that licenses the entity and its pharmacist-in-charge. Its exit — to a chain that buys the prescription files, to a pharmacist-buyer, or to the next generation — is shaped by the LIFO reserve and the S corporation's single tax. Here is the analysis and the estimated taxes.

Small Business Tax

Independent Pharmacy Taxes: The Inventory, the PBM Clawbacks, the DIR Fees, and LIFO for a Drug Shelf That Only Gets More Expensive

September 30, 2026

An independent pharmacy's return is dominated by one number — the cost of drugs dispensed, often 75 to 85 percent of revenue — and shaped by the pharmacy benefit managers who set the reimbursement, then take part of it back months later through fees and clawbacks. Here is the inventory computation, the LIFO election that pharmacies use more than almost any other small business, the PBM fee timing, the DEA and state board compliance, and the front-store line that carries sales tax.

Small Business Tax

Marine Service and Boat Repair Shop Taxes: The Yard, the Travel Lift, Parts and Labor Sales Tax, and the Storm-Season Haul-Outs

September 30, 2026

A marine service shop or boatyard is an auto repair shop on the water: a yard and a travel lift instead of lifts and bays, a parts inventory of engines, drives, and electronics, technicians certified by the engine makers, and a storage business that fills the yard before every hurricane. Here is each deduction, the environmental compliance a waterfront shop carries, the parts-and-labor sales tax split, and the seasonal and storm-driven revenue.

Small Business Tax

Marine Service Business Entity and Estimated Taxes: The Yard in Its Own LLC, the S Election, and the Hurricane That Rewrites the Fourth Quarter

September 30, 2026

A boatyard owner's most valuable asset is usually the waterfront — land that is scarce, appreciating, and exposed to the yard's operating liabilities unless it sits in its own entity. The operating business elects S status on the standard arithmetic, and the estimated taxes follow a season the weather sets: spring commissioning, fall storage contracts, and a hurricane that can rewrite a quarter. Here is both, for a mobile marine technician, a repair shop, and a full-service yard.

Small Business Tax

Medical Spa Entity and Estimated Taxes: The Management Company, the Professional Entity, and the December That Sells Next Year's Treatments

September 30, 2026

A medical spa's entity structure is often two entities — a management company and a physician-owned professional entity — and the tax planning happens inside that structure: the S election for each, the fair-market management fee that moves profit between them, and the QBI deduction that one entity keeps and the other may not. The estimated taxes run on a December that sells next year's packages and gift cards and a device year that erases the tax. Here is both.

Small Business Tax

Medical Spa Taxes: The Medical Director, the Injectables Inventory, the Memberships, and the Corporate Practice Rule

September 30, 2026

A medical spa sits between a medical practice and a retail spa — injectables, lasers, and body treatments delivered under a physician's supervision, sold through memberships and packages, with a retail skincare line — and its tax picture has pieces of both: the state's corporate practice of medicine rules decide who can own it, the injectables are inventory with a cost that dominates the margin, prepaid packages and memberships raise the advance-payment question, and the specified-service label depends on what the business actually does. Here is each deduction and the structural questions.

Small Business Tax

Physician Practice Entity Structure: The Professional Corporation, the Group Practice Rules, the Cash Balance Plan, and the Hospital or Private Equity Offer

September 30, 2026

A physician practice's entity decision is made inside the corporate practice of medicine rules, the Stark law's group practice definition, and a specified-service label that zeroes the QBI deduction — so the planning instruments are the compensation plan, the retirement plan, and the exit: a hospital employment deal, a private equity platform's management services structure, or independence. Here is the analysis for a solo physician, a multi-physician group, and a group weighing an offer.

Small Business Tax

Physician Practice Taxes: Collections Not Charges, the Credit Balances, the Ancillary Services, and the Stark Rules That Shape the Compensation

September 30, 2026

A physician practice's return is collections — the insurers' allowed amounts and the patients' balances, net of contractual adjustments that are never income — against a staff, an EHR, malpractice, and the ancillary services (imaging, lab, infusion, physical therapy) that the federal self-referral and anti-kickback rules constrain. Here is each deduction, the revenue-cycle items that trip up practices' books, and how the Stark rules shape the way physicians in a group can be paid.

Small Business Tax

Property Management Company Deductions: The Trust Account, the Owner Disbursements, the Maintenance Crew, and the 1099s You File for Your Owners

September 30, 2026

A property management company collects rent that isn't its income, pays expenses that aren't its deductions, and files information returns on behalf of owners who never see the tenants. Its own return is management fees, leasing fees, and maintenance markups against a payroll, a fleet of maintenance vehicles, and software. Here is the trust-account discipline, each deduction category, and the 1099 obligations the manager carries for its owners.

Small Business Tax

Property Management Company Entity Structure: The LLC, the S Election, the Brokerage License, and the Door Count a Buyer Pays For

September 30, 2026

A property management company's entity decision runs on the S election arithmetic against a property manager's salary, inside the state's real estate licensing rules — most states require the company or its principal to hold a broker's license — and with an exit market that values the business per door under management. Here is the analysis for a solo manager, a company with staff and a maintenance crew, and an owner planning a sale.

Small Business Tax

Property Management Company Estimated Taxes: Steady Fees, the Leasing Season, and the Year the Management Contracts Were Bought

September 30, 2026

A property management company's income is among the steadiest in small business — a percentage of rent collected every month — with a leasing season that lifts the summer, maintenance billings that follow the weather, and a growth path that often runs through buying another manager's contracts, whose fifteen-year amortization changes the tax. Here is the estimated-tax routine for an S corporation manager and a solo manager on Schedule C.

Small Business Tax

Staffing Agency Entity and Estimated Taxes: The S Election, the Healthcare Line That Needs Its Own Entity, and the Owners' Trust Fund Exposure

September 30, 2026

A staffing agency's entity decision has the usual S election arithmetic on a manager's salary, a specified-service question that depends on which workers it places, and a personal exposure no entity removes: the trust fund recovery penalty for unpaid payroll taxes reaches the owners and officers who control the deposits. The estimated taxes run on a gross margin that swings with the placements and a Work Opportunity credit that lapsed for 2026 hires and may return. Here is both.

Small Business Tax

Staffing Agency Taxes: The Payroll You Carry for Clients, Workers' Compensation by Class Code, the PEO Question, and the Gross-Versus-Net Revenue Line

September 30, 2026

A staffing agency is the employer of workers who work somewhere else: it pays their wages and payroll taxes weekly, carries their workers' compensation by the client's class code, and bills the client a markup weeks later. Its tax picture turns on being the employer of record, on the payroll float, on the difference between temporary staffing and a professional employer organization, and on the specified-service question for the staffing of licensed professionals. Here is each piece.

Cross-Border Tax (U.S.–Canada)

U.S. Citizen Owning a Canadian Corporation: Form 5471, GILTI, Subpart F, and the Section 962 Election

September 30, 2026

A U.S. citizen living in Canada who owns a Canadian-controlled private corporation — the standard structure for a Canadian small business — owns a controlled foreign corporation in the eyes of the IRS: Form 5471 every year, the GILTI inclusion on the company's active profits, subpart F on its passive income, and the section 962 election that can make the U.S. tax on those inclusions workable. Here is each piece and how it meets the Canadian small business deduction.

Small Business Tax

Used Car Dealer Entity and Estimated Taxes: The BHPH Finance Company, the S Election, and the Tax Refund Season That Sells a Quarter of the Year

September 30, 2026

A used car dealer's entity decision often involves two companies — the dealership and a related finance company that holds the buy-here-pay-here notes — and its estimated taxes are shaped by a sales calendar the tax system itself creates: February through April, when customers' tax refunds become down payments. Here is the entity analysis for a retail lot, a BHPH dealer with a related finance company, and the estimated-tax routine built around the refund season.

Small Business Tax

Used Car Dealer Taxes: Floor Plan Interest, Form 8300 for Cash Deals, Buy-Here-Pay-Here Installment Sales, and Inventory That Depreciates on the Lot

September 30, 2026

A used car dealership is an inventory business whose inventory loses value every day on the lot, financed by a floor plan whose interest has its own tax rule, selling to customers who pay cash (Form 8300 at US$10,000), finance through a lender (the dealer reserve), or — at a buy-here-pay-here lot — finance through the dealer itself on installment notes. Here is each: the inventory valuation, the floor plan interest, the Form 8300 obligation, the installment method, the warranties and add-ons, and the sales tax on vehicles.

Small Business Tax

Wedding and Event Venue Deductions: The Deposits a Year Ahead, the Building, the Catering, and the Season That Decides the Year

September 30, 2026

A wedding and event venue sells dates a year or more in advance, collects deposits that are income under the cash method long before the event, and delivers the event with a building, grounds, and often a catering operation — each with its own tax treatment. Here is the deposit timing, the building and land improvements a venue is made of, the catering and bar operation, the vendors the venue pays and the ones it only refers, and the sales tax on a bundled event.

Cross-Border Tax (U.S.–Canada)

Adjusted Cost Base (ACB): How to Calculate It

September 29, 2026

Adjusted cost base explained: what ACB is, the formula (cost plus commissions, adjusted for return of capital, reinvested distributions, and superficial losses), averaging for identical shares, foreign currency, and why a Canadian's ACB and a U.S. resident's basis in the same shares can differ.

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