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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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1,407 guides

Small Business Tax

Auto Repair Shop Entity Structure: The LLC, the S Election, and the Building That Should Be in a Separate Entity

September 29, 2026

An auto repair shop's entity decision has the standard S election arithmetic on a working owner-technician's salary, a liability profile that includes every customer's car in the building, and one structural point most shop owners get wrong: the shop building, when owned, belongs in a separate entity that leases it to the operating company. Here is the analysis for a solo mechanic, a multi-bay shop with technicians, and a shop that owns its real estate.

Small Business Tax

Convert an LLC to a C Corp: Tax Consequences

September 29, 2026

Converting an LLC to a C corporation explained: the three ways to convert, the tax-free incorporation rules under section 351, the liabilities-in-excess-of-basis trap, what happens to the LLC's tax attributes, why startups raising venture capital convert, and when an S election is the better move.

Small Business Tax

Dental Practice Entity Structure: The Professional Corporation, the S Election, and the Specified-Service Phase-Out the Retirement Plan Answers

September 29, 2026

A dentist's entity decision has three fixed points: most states require a dental practice to be owned through a professional corporation or professional LLC owned by licensed dentists; dentistry is a specified service trade, so the QBI deduction phases out at the income most practice owners earn; and the practice's profit is large enough that the S election's payroll-tax saving and a defined benefit plan's six-figure deduction both matter. Here is the analysis for a solo practice, a two-dentist partnership, and a practice preparing to sell to a DSO.

Small Business Tax

E-Commerce Business Entity Structure: The LLC, the S Election, and the Inventory That Sits in Twelve States

September 29, 2026

An e-commerce seller's entity decision has the standard S election arithmetic on an operations manager's salary, a liability profile built around product claims and supplier disputes, and two questions the other trades don't face: the multistate footprint that marketplace fulfillment creates, and the exit market — e-commerce brands are bought and sold on a multiple of earnings, and the entity has to be sellable. Here is the analysis for a solo seller, a brand with employees, and a seller preparing to exit.

Small Business Tax

Food Truck Entity and Estimated Taxes: The LLC, the S Election That Waits, and a Season That Follows the Events

September 29, 2026

A food truck's entity question is the LLC for a business that serves food to the public from a vehicle, and an S election that waits until the profit clears a chef-operator's salary — which for most trucks takes a second truck or a catering line. Its estimated-tax question is a season that follows the events calendar, a first year whose safe harbor comes from the owner's last return, and a truck purchase that erases the tax. Here is both, in one guide, for a solo truck and a two-truck operation with catering.

Small Business Tax

Form 2553: S Election Deadline and Late Election Relief

September 29, 2026

Form 2553 explained: the two-month-and-fifteen-day deadline for an S corporation election, what the form requires, how an LLC files it, the late election relief procedure with reasonable cause, and how to confirm the election was accepted.

Small Business Tax

General Contractor Entity Structure: The LLC, the S Election, and the Bonding Line That Wants a Balance Sheet

September 29, 2026

A general contractor's entity decision is shaped by three things the other trades meet less often: liability that spans every sub's work, a bonding company that wants a corporate balance sheet and a personal guarantee, and a revenue line that is mostly pass-through — so the profit the S election works on is a fraction of the gross. Here is the analysis for a solo remodeler, a residential general with a crew, and a commercial contractor with a surety line.

Small Business Tax

Insurance Agency Entity Structure: The LLC, the S Election, the Carrier Appointments, and the Book That Transfers With the Entity

September 29, 2026

An insurance agency's entity decision runs on standard S election arithmetic — with a payroll that exists once the agency has staff, a producer's salary that the employed market documents, and a QBI deduction that survives because insurance agents are excluded from the specified-service list — plus two features the carriers impose: the agency itself must be licensed and appointed in every state where it writes, and the book of business is worth more inside an entity that can be sold whole. Here is the analysis for a solo producer, a small agency, and an agency planning a sale or perpetuation.

Small Business Tax

IT Services Firm Entity Structure: The LLC, the S Election, the Consulting Line That Needs Its Own Books, and the Technicians in Four States

September 29, 2026

An IT services firm's entity decision has the standard S election arithmetic on a technical director's salary, a liability profile that has changed with cyber risk, and two structural questions the profession raises more than others: whether the advisory practice should be a separate business so the managed-services firm keeps the QBI deduction, and how a remote workforce across several states shapes the entity's registrations. Here is the analysis for a solo consultant, a managed services firm with staff, and a firm whose advisory line has outgrown the de minimis rule.

Small Business Tax

Photography Business Entity Structure: The LLC, the S Election, and the Deposits That Arrive a Year Before the Wedding

September 29, 2026

A photographer's entity decision is the standard S election arithmetic on a working photographer's salary — which for most solo photographers doesn't pay until profit passes six figures — plus a liability profile (a light stand on a guest, a lost wedding's images, a drone) that makes the LLC worth forming early, and a cash pattern (wedding deposits a year ahead) that shapes the estimated taxes more than the entity. Here is the analysis for a solo photographer, a studio with associates, and a commercial photographer with licensing income.

Small Business Tax

Real Estate Agent Entity Structure: The S Corporation, the Commissions Paid to an Entity, and the Brokerage Rule That Varies by State

September 29, 2026

A real estate agent's S election has a prerequisite the other trades don't: the commissions have to be payable to the entity, and whether a brokerage may pay an agent's LLC or professional corporation is a state licensing question. Where it's allowed, the election runs on the standard arithmetic against a producing agent's reasonable salary; where it isn't, the agent stays on Schedule C regardless of profit. Here is the state question, the worksheet, the QBI point for agents above the threshold, and the team structure.

Small Business Tax

Restaurant Entity Structure: The LLC, the S Election, the Owner-Chef, and the Second Location That Needs Its Own Entity

September 29, 2026

A restaurant's entity decision is the standard S election arithmetic on an owner-chef's or general manager's salary, with a liability profile — foodborne illness, dram shop, a kitchen full of employees — that makes the LLC the floor and a second location that should be its own entity. The payroll always exists, the investors often do, and the lease and the liquor license are the entity's. Here is the analysis for a single-location owner-chef, a restaurant with outside investors, and a group with three locations.

Small Business Tax

Roofing Contractor Entity Structure: The LLC, the S Election, and the Workers' Compensation Line That Decides the Arithmetic

September 29, 2026

A roofing contractor's entity decision starts from a liability profile that ends businesses — falls, leaks, storm-season disputes — and a payroll whose workers' compensation cost changes every number in the S election worksheet. The LLC or corporation is the floor; the election pays once profit clears a superintendent's salary; and the crew's classification, which the carrier's audit will test, decides whether the payroll exists. Here is the analysis for a solo roofer, a residential company, and a storm-chasing operation.

Small Business Tax

S Corporation vs LLC: The Tax Differences

September 29, 2026

S corporation vs LLC explained: an LLC is a legal entity and an S corporation is a tax election, how each is taxed by default, the self-employment tax difference, reasonable compensation, the QBI interaction, and when an LLC should elect S status.

Small Business Tax

Salon and Barbershop Entity Structure: The LLC, the S Election, and the Owner Behind the Chair

September 29, 2026

A salon owner's entity decision depends on whether the owner is behind a chair or behind the desk: an owner-stylist's reasonable salary is a working stylist's earnings plus management, which consumes most of a small salon's profit, while an owner who manages a salon of employees has the payroll the S election needs and a manager's salary against a larger distribution. The liability — a chemical burn, a slip, a renter's client — makes the LLC the floor. Here is the analysis for a solo suite, a mixed salon, and an employee salon with retail.

Small Business Tax

Short-Term Rental Entity and Estimated Taxes: The LLC Per Property, the Lender's Consent, and the Season the Bookings Follow

September 29, 2026

A short-term rental host's entity question is mostly liability — an LLC per property, with the mortgage lender's consent — because rental income on Schedule E carries no self-employment tax for an S election to save. The estimated-tax question is a season that follows the destination, platform payouts that arrive after the stay, and a cost-segregation year whose loss can eliminate the host's tax on wages. Here is both, for a single-property host and a multi-property operator with a Schedule C management arm.

Small Business Tax

Tree Service Company Entity Structure: The LLC, the S Election, and the Equipment Loss That Decides the Timing

September 29, 2026

A tree service company's entity decision is governed by the trade's liability (falling limbs, falling climbers), an equipment cycle that can produce a first-year loss larger than the profit, and a crew whose workers' compensation cost changes the S election's arithmetic. The LLC or corporation is the floor; the election waits for the equipment write-offs to clear; and the crew's classification, tested by the carrier's audit, decides whether the payroll exists. Here is the analysis for a climber with a truck, a company with crews, and a storm operation.

Small Business Tax

Trucking Owner-Operator Entity and Estimated Taxes: The LLC, the S Election After the Tractor Is Written Off, and the Weekly Settlement Reserve

September 29, 2026

An owner-operator's entity decision waits for the tractor: the year the truck is expensed produces a loss or a small profit, and the S election's arithmetic only appears once the write-off is gone and the profit shows. The liability — a truck in traffic, a load, a lease with a carrier — makes the LLC the floor. The estimated taxes run on weekly settlements with nothing withheld and a per diem that shrinks the taxable net. Here is both, for a driver leased to a carrier and one running under their own authority with a second truck.

Small Business Tax

Trust Fund Recovery Penalty: Personal Liability Explained

September 29, 2026

The trust fund recovery penalty explained: why unpaid withheld payroll taxes follow the owner personally, who counts as a responsible person, how willfulness is judged, the 100 percent penalty under section 6672, and why an LLC or corporation does not shield it.

Small Business Tax

Electrical Contractor Entity Structure: The LLC, the S Election, and the Apprentices Who Are Employees by Definition

September 28, 2026

An electrical contractor's entity decision starts from a payroll that already exists — journeymen and apprentices are employees, and a registered apprentice is an employee by the program's definition — which makes the S election cheap to add once the owner's profit clears a master electrician's salary. The liability (a fire after a job, a shock on a site) makes the LLC or corporation the floor, and the license itself is often held by a qualifying individual rather than the entity. Here is the analysis for a solo electrician, a service company with crews, and a new-construction contractor.

Small Business Tax

HVAC Company Entity Structure: The S Election, the Installers on Payroll, and the Agreement Base That Changes the Method Question

September 28, 2026

An HVAC company is a payroll business that sells equipment and collects service fees in advance — three facts that shape its entity decision. The technicians and installers are employees, so the S election's payroll already exists; the equipment margin and the agreement base make the profit larger and lumpier than a pure service trade's; and the liability (a carbon monoxide event, a refrigerant release, a rooftop fall) makes the LLC or corporation the floor. Here is the analysis for a one-van operator, a service-and-install company, and a company with a large maintenance base.

Small Business Tax

Landscaping Company Entity Structure: The LLC, the S Election, and a Payroll That Exists From March to November

September 28, 2026

A landscaping company's entity decision turns on a payroll that exists — seasonal crews are employees, hired in spring and laid off in fall — which makes the S election cheap to add once the owner's profit clears a landscape operations manager's salary, and on a liability profile (mowers, chainsaws, chemicals, snow-plowed lots) that makes the LLC or corporation the floor. The seasonal shutdown complicates the owner's salary schedule; the snow side smooths it. Here is the analysis for a solo operator, a seasonal-crew company, and a year-round landscape-and-snow business.

Small Business Tax

Plumbing Company Entity Structure: The LLC for the Water Damage, the S Election, and the Master Plumber's Salary

September 28, 2026

A plumbing company's entity decision is shaped by a license that attaches to a master plumber, a payroll that exists from the first apprentice, and a liability profile whose claims are water — a failed water heater install, a repipe leaking behind a wall, a sewer replacement that fails — which makes the LLC or corporation the floor. The S election is cheap to add once the owner's profit clears a master plumber's salary, and the resale margin makes that profit larger than a pure labor trade's. Here is the analysis for a solo plumber, a service company with crews, and a plumbing-and-drain company with emergency revenue.

Small Business Tax

Pressure Washing Business Entity and Estimated Taxes: A Solo Rig, a Spring-to-Fall Season, and the S Election That Usually Waits

September 28, 2026

A pressure washing or exterior cleaning business is a rig on a trailer, a season that runs spring to fall, and — for most operators — a solo owner whose profit hasn't reached the S election's threshold. The entity question is the LLC for liability (a stripped deck, a blown-out window seal, a chemical runoff complaint) and the S election that usually waits; the estimated-tax question is a season with three quiet months and a reserve that funds them. Here is both, in one guide, for the solo operator and the two-rig company.

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