Taxes

1031 Exchange Related-Party Rules and the Two-Year Holding Requirement How related-party 1031 exchanges trigger automatic disqualification if property is sold within two years, forcing retroactive gain recognition.

1031 Exchange Timeline: 45-Day and 180-Day Rules Explained Understand the strict 45-day identification and 180-day closing deadlines for 1031 exchanges. Miss either window and you lose tax deferral and face capital gains tax.

1031 like-kind exchange A 1031 exchange allows investors to defer capital gains and depreciation recapture by selling one property and buying a similar replacement property within strict timelines.

1031 Like-Kind Exchange: Tax Deferral Mechanics How 1031 like-kind exchanges defer tax on property sales through identification and closing windows, boot rules, and basis carryover.

1033 Like-Kind Exchange Detail Real property swap allowing tax deferral on real estate gains through reinvestment in qualifying replacement property.

3,000 Dollar Capital Loss Deduction The annual cap allowing investors to deduct up to $3,000 of net capital losses against ordinary income.

401k Employer Match Free employer contributions to an employee's 401k retirement plan, typically conditional on the employee deferring a percentage of salary—the largest employer subsidy of retirement saving.

403(b) Plan A workplace retirement plan for public school employees and nonprofit staff with lower regulatory burden than 401(k)s, legacy annuity contracts, and restricted investment menus.

403(b) RMD Rules for Teachers and School Employees How required minimum distribution rules apply to 403(b) plans for teachers and public-school employees, including still-working exceptions.

403(b) vs 457(b): Tax Differences Explained 403(b) and 457(b) plans serve different workers and have distinct contribution limits, early-withdrawal penalties, and required-distribution rules.

457(b) Deferred Compensation Plan A retirement plan for government and nonprofit employees offering the same contribution limits as 401(k)s, no 10% early-withdrawal penalty, and unique Roth conversion advantages.

529 Plan Investment Gains and Tax Rules How earnings grow tax-deferred inside a 529 plan, what triggers a taxable distribution, the 10% penalty on non-qualified withdrawals, and the rollover-to-Roth option.

529 Plan Rollover to Roth IRA: Rules and Limits SECURE 2.0 allows unused 529 plan balances to roll into a Roth IRA subject to a lifetime cap and 15-year seasoning requirement on account funding.

Accumulated Depreciation Real Estate Total depreciation claimed on property that reduces taxable gain upon sale

Additional Medicare Tax for Self-Employed Individuals How the 0.9% additional Medicare tax applies to self-employment income above a threshold. Learn the calculation and how it differs from regular SECA tax.

Additional Medicare Tax Investment Income Threshold: How It Works The additional Medicare tax on investment income applies at $200k/$250k thresholds alongside the 0.9% employee Medicare tax, creating dual obligations for high earners.

Additional Medicare Tax on Wages The 0.9% Medicare surtax on earned income above threshold amounts, separate from the investment-income surtax.

Adjusted Cost Basis How corporate actions, dividends, and improvements modify an asset's original purchase price to determine gain or loss.

After-Tax 401(k) Contributions How the mega-backdoor Roth strategy exploits the gap between employee and plan contribution limits to convert after-tax 401(k) dollars into tax-free Roth savings.

Allocating Tax Basis Between Land and Building Allocating tax basis between land and building splits your purchase price for depreciation; land is never depreciable, building is.

Alternate Valuation Date The executor's discretionary election to value estate assets six months after death, available if the election reduces both gross estate and estate tax.

Alternative Minimum Tax and Incentive Stock Options AMT on incentive stock options can create a tax liability when exercising ISOs, even without selling shares, forcing employees to estimate exposure beforehand.

Alternative Minimum Tax for High-Income Employees Which W-2 income sources and employment deductions most commonly trigger the alternative minimum tax for salaried workers.

Alternative minimum tax for investors The alternative minimum tax is a parallel tax system for high-income taxpayers. Certain deductions and preferences are added back, and the higher of AMT or regular tax is paid.

Alternative Minimum Tax for the Self-Employed Self-employed sole proprietors and partners often encounter AMT through depreciation adjustments, home-office deductions, and timing differences between regular and AMT rules.

AMT and Accelerated Depreciation: When Bonus Depreciation Creates a Preference Item How the spread between regular and AMT depreciation schedules creates an AMT accelerated depreciation preference item that triggers alternative minimum tax.

AMT and Charitable Contribution Deductions Under the AMT, most charitable contribution deductions survive; however, some non-cash donations and deduction-related items are disallowed preference items.

AMT and Long-Term Capital Gains: Do Preferential Rates Still Apply? Understand how AMT and long-term capital gains rates interact—gains keep their preferential rates but erode the exemption phaseout, raising effective tax.

AMT and Nonqualified Stock Options Why nonqualified stock options don't create AMT preference items, unlike ISOs—and how regular income inclusion affects your alternative minimum tax.

AMT and Qualified Dividends: Are They Taxed Differently Under AMT? Explore how qualified dividends interact with the Alternative Minimum Tax, including the role of exemption phaseouts.

AMT and Roth IRA Conversions: Tax Interaction Explained AMT and Roth IRA conversion tax interaction: how a large conversion pushes income into alternative minimum tax territory and how to size conversions to avoid triggering tentative minimum tax.

AMT Credit Carryforward How excess AMT paid in one year becomes a credit that can offset regular tax liability in future years.

AMT Exemption Inflation Adjustments Explained How annual CPI indexing of the AMT exemption amount protects taxpayers from bracket creep and why the 2018 Tax Cuts and Jobs Act changed the formula.

AMT Exemption Phase-Out How the Alternative Minimum Tax exemption shrinks dollar-for-dollar above income thresholds, exposing taxpayers to wider tax exposure.

AMT for Married Filing Separately: Exemption and Rate Rules Married filing separately filers face a halved AMT exemption and steeper phaseout than joint filers. This tax structure creates powerful incentives to file jointly.

AMT for Trusts and Estates: Exemption Amount and Filing Rules How the alternative minimum tax applies to trusts and estates, including compressed income brackets, lower exemption amounts, and planning strategies.

AMT Impact on State and Local Tax Deductions AMT state and local tax deduction impact: how SALT becomes an add-back and interacts with the $10k SALT cap for high-income filers.

AMT Small Business Corporation Exemption The AMT small business corporation exemption exempts qualifying C-corps from the corporate AMT entirely if average gross receipts stay under a three-year threshold.

AMT Tax Preference Items The specific income and deduction adjustments that add back into the Alternative Minimum Tax base, expanding tax liability for high-income earners.

AMT Triggered by Incentive Stock Option Exercise Understand how ISO exercise creates an AMT preference item via the bargain element spread, tax timing strategies, and the mechanics of dual-track taxation.

AMT vs Regular Tax: Which One You Actually Pay Understand how the alternative minimum tax works: you pay whichever is higher—regular income tax or tentative minimum tax. See how the crossover works.

Angel Investor Network Organized groups of high-net-worth individuals pooling capital and expertise to fund early-stage startups at seed and pre-Series A stages.

Annual Exclusion (Gift Tax) Maximum amount an individual can gift tax-free to each recipient per calendar year without filing a gift tax return.

Annuity Exclusion Ratio Tax Calculation How the exclusion ratio determines what portion of annuity payments is tax-free return of capital versus taxable ordinary income.

Annuity Exclusion Ratio: How to Calculate the Tax-Free Portion Learn how to calculate the IRS annuity exclusion ratio to determine the tax-free and taxable portions of each annuity payment.

At-Risk Rules for Investors Tax regulations that limit deductible losses in investment activities to the amount of economic capital a taxpayer has actually invested at risk.

At-Risk Rules for Investors Section 465 at-risk rules limit deductible losses to the amount an investor has economically at stake, capping losses before passive-activity rules apply.

At-Risk Rules for Real Estate How Section 465 limits real estate loss deductions to the amount a taxpayer has economically at stake.

At-Risk Rules for Real Estate Investors How at-risk limitations cap deductible losses to an investor's economic exposure, with exceptions for real estate nonrecourse financing.

Average cost basis Average cost basis is a method of calculating cost basis by averaging the purchase price across all shares owned. It is simple but rarely the most tax-efficient method.

Backdoor Roth IRA and the Pro-Rata Rule Learn how the pro-rata rule applies to backdoor Roth conversions when you hold pre-tax IRA balances, and how to calculate the tax cost of the conversion.

Backdoor Roth Mechanics Contributing to a Roth IRA above income limits via non-deductible traditional IRA contributions and conversion; mechanics and pro-rata rule.

Bargain Sale to Charity A transaction in which appreciated property is sold to a qualified charity below fair-market value, creating both a deductible gift and a taxable capital gain.

Below-Market Loans and Gift Tax Rules Below-market loans trigger imputed gift tax when the interest charged is less than the applicable federal rate, with exceptions for small loans and specific arrangements.

Bond Premium Amortization Tax Treatment Investors who buy taxable bonds above par can elect to amortize the premium, reducing taxable interest income each year and allowing a capital loss on maturity.

Bonus depreciation Bonus depreciation allows businesses to immediately deduct 100% of the cost of eligible property (through 2025), then phases down to 80% (2026), 60% (2027), etc. It accelerates deductions without an annual limit.

Boot in a 1031 Exchange Boot is taxable cash or unlike-property received in a 1031 exchange when replacement property value falls short of relinquished property. Learn how boot triggers gain.

Boot Recognition in Exchange Cash or unlike property received in exchange triggering gain recognition in otherwise tax-deferred transactions.

Capital Gains Netting The IRS ordering rules for offsetting short-term and long-term gains against losses before calculating your tax bill.

Capital Gains on a Home Sale Exceeding the Exclusion How to calculate and report taxable capital gains when a primary residence sale profit exceeds the $250,000 (single) or $500,000 (married) federal exclusion.