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Guides · Tax Planning

Tax Planning guides

167 plain-English guides on tax planning, each one ending in what to do next.

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

Page 2 of 7, newest first.

Tax Planning

Constructive Receipt Doctrine: When Income Is Taxable Even Before You Receive It

Under the constructive receipt doctrine (Treas. Reg. 1.451-2), income is taxable in the year it is credited, set apart. Constructive receipt rules: |.

Sep 5, 2026
Tax Planning

Day Trader Tax Status: Section 475 Mark-to-Market Election and Trader vs. Investor Classification

The tax treatment of trading income depends entirely on whether the IRS classifies you as a trader or an investor. Trader vs.

Sep 5, 2026
Tax Planning

Disabled Access Credit: How Small Businesses Claim Up to $5,000 for ADA Compliance (IRC 44)

The Disabled Access Credit under IRC 44 provides small businesses (30 or fewer full-time employees OR $1 million or less in gross receipts) a tax credit.

Sep 5, 2026
Tax Planning

Domestic Asset Protection Trusts (DAPTs): State Laws, Creditor Protection, and Tax Implications for Business Owners

A domestic asset protection trust (DAPT) is an irrevocable trust established under the laws of a state that permits the grantor to be a discretionary.

Sep 5, 2026
Tax Planning

Tax Benefits of US Manufacturing: Bonus Depreciation, R&D Credits, and State Incentives

US manufacturers benefit from several overlapping tax incentives: 100% bonus depreciation on equipment and machinery (permanently restored under OBBBA).

Sep 5, 2026
Tax Planning

Domestic Production Activities Under OBBBA: What Small Manufacturers Need to Know

The original Section 199 Domestic Production Activities Deduction (DPAD) allowed a 9% deduction on qualified production activities income (QPAI).

Sep 5, 2026
Tax Planning

E-Commerce Tax Obligations: What Online Sellers Must Know

E-commerce sellers face unique tax challenges: multi-state sales tax nexus, inventory accounting, 1099-K reporting from payment processors.

Sep 5, 2026
Tax Planning

Hiring Family Members: Income Splitting, Kiddie Tax, and the Rules for Employing Your Children

Hiring family members in a legitimate business is one of the most effective tax planning strategies for small business owners.

Sep 5, 2026
Tax Planning

General Business Credit: How Tax Credits Work Together and the Carryback and Carryforward Rules Under IRC 38

The general business credit under IRC 38 is not a single credit but an aggregation of over 30 individual business tax credits.

Sep 5, 2026
Tax Planning

Health Insurance Deduction Options for Small Business Owners

Self-employed business owners can deduct health insurance premiums as an above-the-line deduction. Health insurance is one of the largest personal.

Sep 5, 2026
Tax Planning

Self-Employed Health Insurance Deduction: How Business Owners Deduct Premiums Above the Line

Self-employed business owners can deduct health, dental, and vision insurance premiums for themselves and their families as an above-the-line deduction.

Sep 5, 2026
Tax Planning

Health Insurance Options for Self-Employed Business Owners: Marketplace, SHOP, ICHRA, and QSEHRA

Self-employed business owners can deduct health insurance premiums as an above-the-line deduction on Form 1040 (not on Schedule C).

Sep 5, 2026
Tax Planning

Health Savings Accounts (HSAs) for Small Business Owners: Triple Tax Advantage

HSAs offer a triple tax benefit: tax-deductible contributions, tax-free growth, and tax-free withdrawals for medical expenses.

Sep 5, 2026
Tax Planning

Health Savings Account (HSA) Strategy for Small Business Owners

HSAs provide a triple tax benefit: tax-deductible contributions ($4,300 individual, $8,550 family in 2025), tax-free growth.

Sep 5, 2026
Tax Planning

Hiring Family Members: Tax Benefits, Kiddie Tax Rules, and Family Partnership Planning

Hiring family members in a small business can produce significant tax savings when structured properly. Family employment payroll tax exemptions: |.

Sep 5, 2026
Tax Planning

HSA Strategy for Small Business Owners: Triple Tax Advantage (2025)

An HSA paired with a high-deductible health plan offers triple tax savings: contributions are pre-tax, growth is tax-free.

Sep 5, 2026
Tax Planning

HSA for Business Owners: Triple Tax Advantage, Contribution Limits, and Investment Strategy

Health Savings Accounts (HSAs) offer a triple tax benefit: contributions are deductible, growth is tax-free, and qualified withdrawals are tax-free.

Sep 5, 2026
Tax Planning

Tax Planning for High-Income Years: Income Smoothing Strategies

A business owner earning $80,000 most years but $250,000 in one year pays more lifetime tax than one earning $120,000 every year.

Sep 5, 2026
Tax Planning

Tax Treatment of Insurance Claims and Proceeds for Small Businesses

Insurance proceeds received by a business are generally not taxable if they reimburse a deductible loss (replacing destroyed equipment.

Sep 5, 2026
Tax Planning

Involuntary Conversions: Deferring Gain on Insurance Proceeds Under IRC 1033

When business property is destroyed, stolen, or condemned, IRC 1033 lets you defer the gain if you replace the property within the statutory period.

Sep 5, 2026
Tax Planning

IRC 1035 Tax-Free Exchange: How to Swap Life Insurance and Annuity Policies Without Triggering Tax

IRC 1035 allows taxpayers to exchange one life insurance policy, endowment contract. Permitted IRC 1035 exchanges. Covers deductibility rules, policy.

Sep 5, 2026
Tax Planning

IRC 199A QBI Aggregation and Planning: How to Maximize the 20% Pass-Through Deduction

The qualified business income (QBI) deduction under IRC 199A provides a 20% deduction on qualified business income from pass-through entities (S-Corps.

Sep 5, 2026
Tax Planning

IRC 199A Qualified Business Income Deduction: Complete Guide to the 20% Pass-Through Deduction

The IRC 199A QBI deduction lets pass-through owners deduct up to 20% of qualified income, subject to W-2 wage and SSTB limitations above the threshold.

Sep 5, 2026
Tax Planning

Tax Planning for Medical and Dental Practices: Entity Structure, Equipment, and Retirement Strategies

Medical and dental practices get the biggest tax savings from an S-Corp election, a defined benefit plus 401(k) combination, and Section 179 on equipment.

Sep 5, 2026