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.
October 4, 2026
Divorce and a closely held business: tax-free transfers under Section 1041 and carryover basis, valuation and the built-in gain the receiving spouse inherits, buyouts funded by the owner or redeemed by the company, S corporation eligibility, retirement accounts and qualified domestic relations orders, alimony after 2018, filing status, and nondeductible legal fees.
Read more →October 4, 2026
Tax deductions for dog walkers and pet sitters: mileage between clients as the largest deduction, platform commissions and Forms 1099-K, liability and bonding insurance, supplies and pet first aid certification, the home office, overnight sits at a client's home, boarding in the sitter's own home and the home-use allocation, and why none of it is taxable in Florida.
Read more →October 4, 2026
Entity structure and estimated taxes for dog walking and pet sitting businesses: the sole proprietor and when the LLC is worth it, why the S election rarely pays until there are walkers on staff, classifying walkers who take your clients, estimated taxes with Thanksgiving, Christmas, and summer peaks, deposits for holiday bookings, and a percentage of every app payout moved to a tax account.
Read more →October 4, 2026
Donor acknowledgment and quid pro quo disclosure: the written acknowledgment for contributions of $250 or more, required contents, timing, quid pro quo statements for payments over $75, good-faith estimates, token and membership exceptions, noncash gifts and Form 8283, vehicle donations, and penalties.
Read more →October 4, 2026
Tax deductions for drone service businesses: aircraft, sensors, and controllers as equipment, batteries and propellers as supplies, the remote pilot certificate and recurrent training, aviation liability insurance, mapping and editing software, vehicle travel to sites, waivers and airspace authorizations, income from real estate, inspection, agriculture, and mapping work, and Florida sales tax on photographs delivered as tangible media versus electronically.
Read more →October 4, 2026
Entity structure and estimated taxes for drone service businesses: the LLC for aircraft liability, the side pilot who covers the tax through paycheck withholding, the full-time operator's sole proprietorship, when a recurring inspection or mapping contract supports the S election, pilots as employees or contractors, estimated taxes on project income, and multistate work under one federal certificate.
Read more →October 4, 2026
Tax deductions for a roll-off dumpster rental business: containers as seven-year equipment, hook-lift and roll-off trucks with full first-year depreciation and the heavy highway use tax, landfill and transfer station tipping fees, fuel, drivers as employees, overweight and prohibited-item charges as income, container deposits, insurance, and why Florida treats a standard roll-off fee as an untaxed waste removal service unless the customer controls the container.
Read more →October 4, 2026
Entity structure and estimated taxes for a roll-off dumpster business: the LLC for the cracked driveway and the hazardous load, the S election once container income exceeds a dispatcher-owner's salary, the construction and renovation cycle that drives demand, estimated taxes in the year a fleet expansion wipes out taxable income, drivers on payroll, and selling the containers and the customer list.
Read more →October 4, 2026
Early retirement withdrawals: the 10 percent additional tax, exceptions by account type (age 55 separation, disability, medical costs, birth or adoption, emergency, domestic abuse, terminal illness, first home, education, health insurance), substantially equal periodic payments, 401(k) loans, and Roth contribution access.
Read more →October 4, 2026
The economic substance doctrine under Section 7701(o): the two-part test (meaningful change in economic position and a substantial non-tax purpose), the 20 and 40 percent strict-liability penalties, where it is applied (shelters, circular transactions, micro-captives, basis-shifting), related doctrines, and the business decisions it does not reach.
Read more →October 4, 2026
Education and training deductions for business owners: the maintain-or-improve-skills test, the new-trade exclusion, continuing education and license renewals, conferences and travel, MBA and degree programs, employer education assistance up to $5,250, and the lifetime learning credit.
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Employee retention credit status in 2026: the claim deadlines that have passed, the 2025 law's bar on late 2021 claims and six-year assessment period, IRS processing and denials, audits and clawbacks with interest, the wage deduction adjustment, and what to do with a pending claim.
Read more →October 4, 2026
Employee versus independent contractor: the IRS behavioral, financial, and relationship factors, state ABC tests, Form SS-8, misclassification costs, Section 530 relief, and the voluntary settlement program.
Read more →October 4, 2026
Estate and gift tax planning for business owners after the 2025 law: the $15 million exemption and portability, the annual exclusion, lifetime gifts versus stepped-up basis, valuation discounts, Form 709, Section 6166 deferral, and state estate taxes.
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Tax deductions for event and wedding planners: vendor payments as pass-through or as gross income depending on who contracts with the vendor, travel and site visits, the home office, planning software and subscriptions, samples and styled shoots as marketing, the $25 client gift limit, meals with clients and vendors, liability insurance, assistants and day-of staff, and Florida sales tax when a planner resells rentals.
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Entity structure and estimated taxes for event and wedding planners: the LLC for the vendor who doesn't show, the S election once profit exceeds a planner's salary, whether planning is a specified service business, deposits received a year ahead and the reserve for them, estimated taxes on a Florida season that runs October through May, day-of staff and payroll, and the client-fund account.
Read more →October 4, 2026
Farm tax deductions on Schedule F: the cash method and prepaid feed and seed, raised versus purchased livestock, equipment and single-purpose structures, soil and water conservation, crop insurance deferral, income averaging, the off-road fuel tax credit, and Florida's agricultural classification and sales tax exemption.
Read more →October 4, 2026
Farm entity structure and estimated taxes: sole proprietorship on Schedule F, the LLC, when an S corporation fits a farm, keeping land in a separate entity, the special estimated tax rule for farmers (one January payment or file by March 1), income averaging, and passing the farm to the next generation.
Read more →October 4, 2026
Tax deductions for fence installation contractors: materials as the contractor's own purchases under Florida's real property rule, augers, post drivers, and trailers as equipment, trucks, crews as employees under the construction workers' compensation rule, permits and local licensing, deposits and progress payments, warranty repairs, and the post-storm surge.
Read more →October 4, 2026
Entity structure and estimated taxes for fence installation companies: the LLC for the fence on the wrong lot, the S election once profit exceeds a foreman's salary, Florida's construction classification and the owner's exemption, deposits and the cash method, estimated taxes through a hurricane surge, subcontracting to general contractors, and the lump-sum versus retail-plus-installation contract classification.
Read more →October 4, 2026
First-year tax checklist for a new business: entity and EIN, bank and bookkeeping, accounting method, startup cost election, estimated taxes, S election timing, sales tax and local registrations, Florida filings, 1099s, retirement plan, and record retention.
Read more →October 4, 2026
Fixing a wrong or missed Canadian departure year: establishing the real date, amending returns and reclaiming tax paid as a resident, late Form T1161 and the penalty, departure tax recalculation, the voluntary disclosures program, and aligning the U.S. residency start date.
Read more →October 4, 2026
Dealer versus investor status in real estate: property held for sale to customers, ordinary income and self-employment tax on flips and wholesale assignment fees, the factors courts use, loss of 1031 and installment treatment, separating flipping and rental activities, and entity choices.
Read more →October 4, 2026
Tax deductions for carpet, tile, and commercial floor care businesses: truck-mounted and portable extractors, buffers, burnishers, and auto-scrubbers as equipment, cleaning chemicals and pads as supplies, vans, crews working nights as employees, recurring commercial contracts, franchise fees, insurance, and Florida's sales tax on nonresidential hard-floor care versus exempt carpet cleaning and residential work.
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