Tax Strategies | Timothy LeGendre CPA

Tax StrategiesHow specific tax provisions actually work, who they apply to, what they require, and where they go wrong. Written and cited by a Florida CPA.What is in this libraryEach page explains the mechanism of a specific tax provision: how it works, who it applies to, what it requires, what you would need to document, and the ways it commonly fails. Projected savings and step-by-step instructions are deliberately left out, because both depend on facts I would need to review first.Rule 72(t) and SEPP DistributionsHow Rule 72(t) lets an IRA or plan owner under 59 1/2 avoid the 10% early distribution tax through SEPP, and where these plans break. Read more at https://timcpa.com/resources/strategies/72t-sepp-early-distributionsThe Section 83(b) Election on Equity CompensationHow a section 83(b) election taxes restricted stock and early-exercised options at grant, not vesting, and why the 30-day deadline has no exceptions. Read more at https://timcpa.com/resources/strategies/83b-election-equity-compABLE Accounts (Section 529A)How an ABLE account under Section 529A builds tax-free savings that mostly stay disregarded for SSI and Medicaid, and where families get it wrong. Read more at https://timcpa.com/resources/strategies/able-accountsAccountable Plan Reimbursements (Section 62(c))How a written accountable plan lets a business reimburse an S-corp owner's home office, vehicle, and phone costs tax-free under Section 62(c). Read more at https://timcpa.com/resources/strategies/accountable-plan-reimbursementsEmployer Adoption Assistance vs. the Adoption CreditHow the Section 137 employer adoption assistance exclusion and the Section 23 adoption credit coordinate, who qualifies, and where the S-corp trap bites. Read more at https://timcpa.com/resources/strategies/adoption-assistance-137Bargain Sales, Gift Annuities and Pooled Income FundsHow a bargain sale, a charitable gift annuity, and a pooled income fund work, who qualifies, and where each one goes wrong in practice. Read more at https://timcpa.com/resources/strategies/advanced-charitable-vehiclesAmended Returns: 1040-X, Superseding Returns, and AARsWhen a filed return needs correcting: Form 1040-X, a superseding return, the partnership AAR rule, or Form 3115, and the refund statute that gates it. Read more at https://timcpa.com/resources/strategies/amended-returnsAnnual Gifting and the Lifetime ExemptionHow the per-donee annual gift tax exclusion and the lifetime estate exemption work together, and where the IRS actually challenges a gifting plan. Read more at https://timcpa.com/resources/strategies/annual-gifting-lifetime-exemptionFlorida Asset Protection: Titling, LLCs, and HomesteadHow Florida homestead, tenancy by the entireties, retirement exemptions, and LLC charging-order law decide what a creditor can reach. Read more at https://timcpa.com/resources/strategies/asset-protectionIRS Audit DefenseWhat actually happens in an IRS audit: who carries the burden of proof, what the Cohan rule can estimate, and the deadline that cannot be extended. Read more at https://timcpa.com/resources/strategies/audit-defenseThe Augusta Rule (Section 280A(g))How Section 280A(g) lets an owner rent a personal residence to their own business for 14 days or fewer, and what the IRS actually attacks. Read more at https://timcpa.com/resources/strategies/augusta-ruleThe Backdoor Roth IRAHow the backdoor Roth IRA works above the income limit, and why the pro-rata rule taxes most of the conversion when other pretax IRAs exist. Read more at https://timcpa.com/resources/strategies/backdoor-rothBoard of Directors and Advisory Board DeductionsA genuine board of directors or advisory board opens deductible director fees, travel, and meeting costs under Section 162, and draws real IRS scrutiny. Read more at https://timcpa.com/resources/strategies/board-of-directors-advisorsBonus Depreciation (Section 168(k))How Section 168(k) bonus depreciation works, which property actually qualifies, and where the 2025 to 2026 acquisition-date transition trips people up. Read more at https://timcpa.com/resources/strategies/bonus-depreciationBuying a Business: Asset Purchase vs. Stock PurchaseWhy a buyer almost always wants an asset purchase over a stock purchase, and the elections that let a stock deal reach the same result. Read more at https://timcpa.com/resources/strategies/business-acquisition-buy-sideThe Business Travel Deduction (Section 162(a)(2))How Section 162(a)(2) lets a business deduct travel costs, what away from home requires, and the recordkeeping mistakes that lose the deduction. Read more at https://timcpa.com/resources/strategies/business-travelBusiness Vehicle DepreciationHow the 6,000-pound weight line, Section 179, and bonus depreciation decide what a business vehicle deducts in year one, and where it goes wrong. Read more at https://timcpa.com/resources/strategies/business-vehicleBuy-Sell Agreement Tax DesignHow a buy-sell agreement's structure decides who gets a basis step-up, and what Connelly v. United States changed for life-insurance funding in 2024. Read more at https://timcpa.com/resources/strategies/buy-sell-agreement-tax-designC-Corp Long-Term Care Insurance (Section 7702B)Why a C corporation can deduct and exclude long-term care insurance premiums for an owner-employee in full, with no age-based dollar cap. Read more at https://timcpa.com/resources/strategies/c-corp-ltc-insuranceLate S-Corp Election Relief for an Existing C CorpHow Rev. Proc. 2013-30 lets a C corp fix a missed S election retroactively, the consistency gate most likely to defeat a request, and what it requires. Read more at https://timcpa.com/resources/strategies/c-corp-to-s-corp-late-electionC Corporation Uses and TrapsWhy a flat 21 percent rate and the QSBS exclusion can beat pass-through taxation, and the double tax, accumulated earnings tax, and PHC tax that erode it. Read more at https://timcpa.com/resources/strategies/c-corp-uses-and-trapsCapital Gains Rate Planning (Section 1(h))How the 0% capital gains bracket, the loss-only wash-sale rule, the NIIT floor, and Medicare and ACA cliffs interact when timing a gain. Read more at https://timcpa.com/resources/strategies/capital-gains-rate-planningCarried Interest and the Section 1061 Three-Year RuleHow section 1061 recharacterizes carried interest gain as short-term within three years, and why rental-property sales usually fall outside it. Read more at https://timcpa.com/resources/strategies/carried-interests-1061Cell Phone and Technology DeductionsHow a business-owned phone, a self-employed owner's personal phone, and an S-corp accountable-plan reimbursement are each taxed, and where each one fails. Read more at https://timcpa.com/resources/strategies/cell-phone-technologyCharitable Bunching and Donor-Advised FundsHow bunching several years of charitable giving into a donor-advised fund, layered with appreciated stock or a QCD, clears the standard deduction. Read more at https://timcpa.com/resources/strategies/charitable-bunching-dafThe Charitable Lead Trust (CLAT and CLUT)How a charitable lead trust pays a charity first and freezes what passes to my client's children, and where a CLAT's zeroed-out design can fail. Read more at https://timcpa.com/resources/strategies/charitable-lead-trustThe Charitable Remainder Trust (CRT)How an irrevocable charitable remainder trust sells an appreciated asset tax-free, pays income for life, and defers gain instead of eliminating it. Read more at https://timcpa.com/resources/strategies/charitable-remainder-trustSpecial Allocations Under Section 704(b) and 704(c)How targeted allocations, nonrecourse debt, and the three Section 704(c) methods decide whether a partnership's special allocations actually hold up. Read more at https://timcpa.com/resources/strategies/complex-704b-and-704c-allocationsCost SegregationHow a cost segregation study reclassifies building components into shorter depreciation lives, and why the passive loss rules decide whether it helps. Read more at https://timcpa.com/resources/strategies/cost-segregationCrop Insurance and Disaster Payment DeferralHow sections 451(f), 451(g), and 1033(e) let a cash-method farm defer or avoid tax on crop insurance proceeds and weather-driven livestock sales. Read more at https://timcpa.com/resources/strategies/crop-insurance-disaster-deferralThe De Minimis Safe Harbor ElectionHow the de minimis safe harbor lets a business expense low-cost equipment outright under a per-item dollar ceiling instead of depreciating it. Read more at https://timcpa.com/resources/strategies/de-minimis-safe-harbor-repair-regsDefined Benefit / Cash Balance PlanHow a defined benefit or cash balance plan lets an older, high-income owner deduct far more than a 401(k) alone, funded by an actuary each year. Read more at https://timcpa.com/resources/strategies/defined-benefit-cash-balanceDelaware Statutory Trust (DST) 1031 Replacement PropertyHow Rev. Rul. 2004-86 lets a Delaware statutory trust interest qualify as 1031 replacement property, and where DST offerings fail that test. Read more at https://timcpa.com/resources/strategies/delaware-statutory-trust-1031Dependent Care FSA vs. the Dependent Care CreditHow the Section 129 Dependent Care FSA and the Section 21 credit compare, who each is open to, and why the two benefits cannot share a dollar of expense. Read more at https://timcpa.com/resources/strategies/dependent-care-fsa-vs-creditDepreciation and RecaptureHow real estate depreciation works under MACRS, and why the recapture at sale splits between a maximum 25 percent rate and ordinary income. Read more at https://timcpa.com/resources/strategies/depreciation-and-recaptureDirect Primary Care and HSA Eligibility (Section 223)How a 2025 law stopped a direct primary care membership from blocking HSA eligibility, and the separate rule for paying its fee tax-free from the HSA. Read more at https://timcpa.com/resources/strategies/direct-primary-care-hsaThe Disabled Access Credit and Section 190 DeductionHow the Section 44 credit and Section 190 deduction combine to offset ADA accessibility costs, and why the Tax Court has actually denied these claims. Read more at https://timcpa.com/resources/strategies/disabled-access-credit-44Earnouts and Rollover Equity in a Business SaleHow an earnout's contingent-payment tax rules differ from rollover equity's section 721 or 351 deferral, and why a rollover never shelters the cash. Read more at https://timcpa.com/resources/strategies/earnouts-and-rollover-equityEducation Tax Credits and 529 PlansHow the American Opportunity Credit, the Lifetime Learning Credit, and 529 plans coordinate without double-dipping, and where each one gets examined. Read more at https://timcpa.com/resources/strategies/education-credits-529sThe Employer-Provided Child Care Credit (Section 45F)How the section 45F credit pays employers for child care costs, why the tentative minimum tax shrinks what lands, and what Florida licensing requires. Read more at https://timcpa.com/resources/strategies/employer-childcare-credit-45fBusiness Energy Tax Credits and DeductionsBusiness energy tax credits and deductions after the 2025 tax law: which ones already closed, and the one investment credit still open to a new project. Read more at https://timcpa.com/resources/strategies/energy-creditsChoosing an Entity: Sole Prop, S-Corp, or C-CorpHow sole proprietorship, S-corp, and C-corp taxation compare, what each election requires, and the failure modes that erode the benefit of choosing one. Read more at https://timcpa.com/resources/strategies/entity-choice-decision-treeThe ESOP Section 1042 RolloverHow section 1042 lets a C-corp owner sell stock to an ESOP, defer the capital-gains tax, and make that deferral permanent by holding to death. Read more at https://timcpa.com/resources/strategies/esop-1042-rolloverThe Estimated Tax Safe Harbor (Section 6654)How the IRC 6654 estimated tax safe harbor works: the 90 and 110 percent tests, the four due dates, and the mistakes that trigger the penalty. Read more at https://timcpa.com/resources/strategies/estimated-taxes-safe-harborFarm Income Averaging (Section 1301)Section 1301 lets a farmer or commercial fisherman recompute a spike year's tax using three prior years' brackets, without moving any income or cash. Read more at https://timcpa.com/resources/strategies/farm-income-averagingFlorida's Agricultural Classification (Greenbelt Law)Florida assesses genuinely farmed or ranched land at agricultural use value, not market value, under Fla. Stat. 193.461. Deadlines, and what can cost it. Read more at https://timcpa.com/resources/strategies/farm-property-tax-greenbelt-flFarm Taxation Essentials (Schedule F)Schedule F farm taxation: what counts as farming, how self-employment tax works, the section 183 hobby-loss test, and how a farm loss is limited. Read more at https://timcpa.com/resources/strategies/farm-taxation-essentialsThe FICA Tip Credit (Section 45B)How the section 45B credit refunds an employer's own FICA match on tip income, why Florida wages clear the floor, and where the math goes wrong. Read more at https://timcpa.com/resources/strategies/fica-tip-credit-45bFiling Status Optimization: MFJ, MFS, or Head of HouseholdHow I decide between married filing jointly, married filing separately, and head of household, the tests each one requires, and where they go wrong. Read more at https://timcpa.com/resources/strategies/filing-status-optimizationFringe Benefit Stacking for S-Corp OwnersHow Sections 127, 79, 132, and 137 let an S-corp stack tax-free fringe benefits, and why family attribution locks some of them away from the owner. Read more at https://timcpa.com/resources/strategies/fringe-benefit-stackingThe Intentionally Defective Grantor Trust (IDGT)How a sale to an intentionally defective grantor trust freezes appreciation and moves it out of an estate, and where the IRS actually challenges it. Read more at https://timcpa.com/resources/strategies/grantor-trust-idgtThe Grantor Retained Annuity Trust (GRAT)How a GRAT lets my client freeze an appreciating asset's value for family at a near-zero taxable gift, and why dying mid-term can undo the whole benefit. Read more at https://timcpa.com/resources/strategies/gratHiring Your Spouse (Section 105 Plan)How putting your spouse on payroll opens Social Security credit, a solo 401(k) slot, an HSA, and a Section 105 plan that deducts family medical costs. Read more at https://timcpa.com/resources/strategies/hiring-your-spouseThe Historic Rehabilitation Tax Credit (Section 47)How the Section 47 credit for rehabilitating a certified historic building works, why it is claimed over five years, and who Section 469 lets use it. Read more at https://timcpa.com/resources/strategies/historic-rehabilitation-credit-47The Hobby-Loss Safe Harbor (Section 183)How the section 183 hobby-loss rule caps deductions at gross income, who it reaches, and why losing the profit-motive fight costs more than it used to. Read more at https://timcpa.com/resources/strategies/hobby-loss-safe-harbor-183The Home Office Deduction (Section 280A)How Section 280A gates the home office deduction, why S-corp owners need an accountable plan instead of rent, and where the position fails. Read more at https://timcpa.com/resources/strategies/home-office-deductionHRA, QSEHRA, and ICHRA: Tax-Free Health ReimbursementHow the HRA, QSEHRA, and ICHRA structures reimburse medical costs tax-free, who actually qualifies for each one, and why a 2%-plus S-corp owner cannot. Read more at https://timcpa.com/resources/strategies/hra-qsehra-ichraHealth Savings Accounts (HSA)How IRC section 223 gives a Health Savings Account its triple tax break, who is eligible, how S-corp ownership changes the mechanics, and where it fails. Read more at https://timcpa.com/resources/strategies/hsaTiming Income and Deductions at Year-EndHow constructive receipt, assignment of income, and economic performance set the real limits on shifting income or deductions across a year-end. Read more at https://timcpa.com/resources/strategies/income-deduction-timing-playbookInstallment Sales (Section 453)How the installment method under section 453 defers gain on a seller-financed sale, and where the 453A interest charge and related-party rules bite. Read more at https://timcpa.com/resources/strategies/installment-salesInterest Tracing Rules (Temp. Reg. 1.163-8T)How Temp. Reg. 1.163-8T decides whether interest on borrowed money is deductible, based on what the funds paid for, not what secures the loan. Read more at https://timcpa.com/resources/strategies/interest-tracing-rulesIRMAA Surcharge Planning (Medicare Part B/D)How the Medicare IRMAA surcharge prices income from two years earlier, who it reaches, and where the life-changing-event appeal actually helps. Read more at https://timcpa.com/resources/strategies/irmaa-surcharge-planningIrrevocable Trusts and the Estate Tax FreezeHow an irrevocable trust freezes estate value for good, why grantor and non-grantor trusts are taxed differently, and where retained control undoes it. Read more at https://timcpa.com/resources/strategies/irrevocable-trust-basicsThe Kiddie Tax (Section 1(g))How section 1(g) taxes a child's unearned income above an annual floor at the parent's own rate, and why a child's wages sit entirely outside it. Read more at https://timcpa.com/resources/strategies/kiddie-taxLate-Election Relief: Rev. Proc. 2013-30 and Section 9100How Rev. Proc. 2013-30 and Section 9100 relief fix a missed tax election, which track applies, and where a discretionary request gets denied. Read more at https://timcpa.com/resources/strategies/late-election-reliefLLC Tax Classification: How Check-the-Box Actually WorksHow an LLC's liability shield and its federal tax classification are separate questions, and how the married-couple default trips Florida owners up. Read more at https://timcpa.com/resources/strategies/llc-basicsThe Family Management CompanyHow an S corporation pays a management company for real services, so the non-corporate entity can employ the owner's kids without withholding FICA. Read more at https://timcpa.com/resources/strategies/management-family-office-companyBusiness Meals Deduction (50% vs. 100%)How Section 274 sorts every business meal into a 50%, 100%, or 0% deduction, and what the 2026 OBBBA rules take away from employer-paid meals. Read more at https://timcpa.com/resources/strategies/meals-deductionThe Mega-Backdoor RothHow the after-tax bucket in a 401(k) fills to the plan's overall Section 415(c) limit and converts to Roth, and why most plan documents cannot do it. Read more at https://timcpa.com/resources/strategies/mega-backdoor-rothNet Unrealized Appreciation (NUA)How the section 402(e)(4) election taxes only plan basis on employer stock now and defers the built-in gain to long-term capital gains rates later. Read more at https://timcpa.com/resources/strategies/net-unrealized-appreciationThe Excess Business Loss Limitation (Section 461(l))How Section 461(l) caps a business loss each year and how the disallowed amount converts into a Section 172 net operating loss carryforward instead. Read more at https://timcpa.com/resources/strategies/nol-excess-business-loss-planningNonqualified Deferred Compensation (Section 409A)How a nonqualified deferred compensation plan under Section 409A defers a key employee's tax, and why it does nothing for an S-corp owner's own pay. Read more at https://timcpa.com/resources/strategies/nqdc-deferred-compOpportunity Zones (Qualified Opportunity Funds)How a Qualified Opportunity Fund defers and excludes capital gain, what changes under the new OZ 2.0 rules, and where the regime-timing trap sits. Read more at https://timcpa.com/resources/strategies/opportunity-zonesThe Paid Family and Medical Leave Credit (Section 45S)How the section 45S credit pays an employer for its own paid leave policy, why Florida keeps the whole benefit, and where the written policy fails. Read more at https://timcpa.com/resources/strategies/paid-family-medical-leave-credit-45sPartial Asset Disposition ElectionHow Treas. Reg. section 1.168(i)-8 lets a rental owner write off a retired roof or HVAC system as an ordinary loss instead of depreciating a ghost asset. Read more at https://timcpa.com/resources/strategies/partial-asset-disposition-electionPartnership Taxation for a Multi-Member LLCHow a multi-member LLC is taxed as a partnership by default, what it can do that an S corporation cannot, and where self-employment tax stands unsettled. Read more at https://timcpa.com/resources/strategies/partnership-multi-member-llcPassive Activity Loss Rules (Section 469)How Section 469 limits rental and business losses to passive income, and when the $25,000 allowance or a fully taxable sale releases them. Read more at https://timcpa.com/resources/strategies/passive-activity-loss-rulesIRS Penalty AbatementWhen an IRS penalty can be removed through First-Time Abate or reasonable cause, what each one requires, and the mistakes that get a claim denied. Read more at https://timcpa.com/resources/strategies/penalty-abatementPrepaid Farm Expenses (Section 464)How IRC section 464 caps a cash-method farmer's prepaid feed, seed, and fertilizer deduction at 50 percent, and when that cap disappears entirely. Read more at https://timcpa.com/resources/strategies/prepaid-farm-expensesPrivate Foundations: What Family Control Really CostsHow a private foundation's five excise taxes and basis-limited stock deduction compare to a donor-advised fund, and where family control goes wrong. Read more at https://timcpa.com/resources/strategies/private-foundationPass-Through Entity Tax (PTET): The SALT Cap WorkaroundHow a state lets a pass-through entity pay its own income tax, turning a capped, itemized SALT deduction into an uncapped federal one, and where it fails. Read more at https://timcpa.com/resources/strategies/ptet-salt-workaroundQBI Deduction Planning (Section 199A)How the Section 199A wage limit, the SSTB self-rental taint, and S-corp salary choices interact, and where the planning around them breaks down. Read more at https://timcpa.com/resources/strategies/qbi-deductionThe QSBS Gain Exclusion (Section 1202)How section 1202 lets a non-corporate shareholder exclude gain on qualifying C-corp stock, and how the 2025 law changed the holding-period tiers and caps. Read more at https://timcpa.com/resources/strategies/qsbs-section-1202Qualified Charitable Distributions (Section 408(d)(8))How a qualified charitable distribution lets an IRA owner 70½ or older send money straight to charity, excluded from income rather than deducted. Read more at https://timcpa.com/resources/strategies/qualified-charitable-distributionsReal Estate Professional Status (REPS)How IRC section 469(c)(7) lifts the automatic passive label from rental real estate, the two tests it requires, and how the IRS actually challenges it. Read more at https://timcpa.com/resources/strategies/real-estate-professional-statusReasonable Compensation DocumentationThe reasonable-compensation documentation an S-corp owner needs: a method report, a duties and hours record, and minutes dated before the payroll runs. Read more at https://timcpa.com/resources/strategies/reasonable-comp-documentationChoosing a Retirement Plan for Your BusinessHow a SEP-IRA, Solo 401(k), SIMPLE IRA, and defined-benefit or cash-balance plan compare, and which one fits based on headcount and income. Read more at https://timcpa.com/resources/strategies/retirement-plan-decision-treeSmall Employer Retirement Plan Credits (Sections 45E and 45T)How the section 45E startup-cost and contribution credits and the section 45T auto-enrollment credit work, and which ones reach a one-participant plan. Read more at https://timcpa.com/resources/strategies/retirement-plan-startup-credit-45e-45tThe Revocable Living Trust (RLT)How a revocable living trust avoids Florida probate and manages incapacity, why it saves no income or estate tax, and where funding it goes wrong. Read more at https://timcpa.com/resources/strategies/revocable-living-trustROBS: Rollovers as Business StartupsHow a new C corporation and 401(k) let a founder roll retirement funds into an active business without current tax or an early-withdrawal penalty. Read more at https://timcpa.com/resources/strategies/robsRoth ConversionsHow a Roth conversion moves pretax IRA money into a Roth by paying tax now, and why the pro-rata rule, the five-year clocks, and IRMAA can undo it. Read more at https://timcpa.com/resources/strategies/roth-conversionsThe S-Corp Owner Comp StackHow the S-corp salary decision drives FICA, the Section 199A deduction, and Solo 401(k) room at once, and where raising or lowering it backfires. Read more at https://timcpa.com/resources/strategies/s-corp-owner-comp-stackS-Corp Reasonable CompensationHow the reasonable-compensation rule forces an S-corp owner to pay W-2 wages before distributions, and what four decided cases say about it. Read more at https://timcpa.com/resources/strategies/s-corp-reasonable-compensationS-Corp Shareholder Health Insurance (Section 162(l))How a more-than-2% S-corp shareholder gets health premiums onto Schedule 1 through W-2 wages, and where that payroll step goes wrong. Read more at https://timcpa.com/resources/strategies/s-corp-shareholder-health-insuranceS-Corp Salary vs. Distribution OptimizationHow the split between S-corp W-2 wages and distributions cuts FICA, why Section 199A can flip the incentive, and what the IRS actually attacks. Read more at https://timcpa.com/resources/strategies/salary-vs-distribution-optimizationSection 1031 Like-Kind ExchangeHow a section 1031 exchange defers capital gains and depreciation recapture on real property, and why personal property no longer qualifies. Read more at https://timcpa.com/resources/strategies/section-1031-like-kind-exchangeThe Section 105 Medical Reimbursement PlanHow a Section 105 plan lets a sole proprietor hire a spouse and deduct the family's medical costs as a business expense, and why it fails inside an S corp. Read more at https://timcpa.com/resources/strategies/section-105-planSection 1244 Stock: Ordinary Loss on Small Business StockHow Section 1244 turns a loss on qualifying small business stock into an ordinary loss instead of a capital one, and who is permanently locked out. Read more at https://timcpa.com/resources/strategies/section-1244-stockSection 179 Expensing: The Election and Its LimitsHow the Section 179 election works item by item, why it cannot create a loss, and where it fails: placed-in-service dates, the SUV cap, recapture. Read more at https://timcpa.com/resources/strategies/section-179-expensingSelf-Directed IRA and Solo 401(k)How a self-directed IRA or solo 401(k) holds real estate and private deals, what Section 4975 forbids, and when income inside the account is taxed. Read more at https://timcpa.com/resources/strategies/self-directed-ira-401kThe Self-Rental Trap (Treas. Reg. 1.469-2(f)(6))How the self-rental rule turns rent paid between an owner's own entities into non-passive income, while a loss on that same rental stays stuck as passive. Read more at https://timcpa.com/resources/strategies/self-rental-trapSelling a Business: Capital-Gains Tax OptionsHow entity type and asset-versus-stock structure decide the tax on a business sale, from personal goodwill to the built-in-gains trap for S corporations. Read more at https://timcpa.com/resources/strategies/selling-a-business-capital-gainsThe SEP IRA (Section 408(k))How the SEP IRA lets a self-employed owner deduct an effective 20% of net self-employment earnings, who it fits, and where it goes wrong. Read more at https://timcpa.com/resources/strategies/sep-iraThe Short-Term Rental Loophole (The 7-Day Rule)An average guest stay of seven days or less means a property is not a rental activity at all. What that changes, what it requires, and where it fails. Read more at https://timcpa.com/resources/strategies/short-term-rental-loopholeThe SIMPLE IRA (Section 408(p))How a SIMPLE IRA works under Section 408(p), why the employer contribution is mandatory every year, and how the two-year rule traps an early rollover. Read more at https://timcpa.com/resources/strategies/simple-iraSpousal Lifetime Access Trust (SLAT)How a spousal lifetime access trust moves assets out of one spouse's estate while the household keeps indirect access through the other spouse. Read more at https://timcpa.com/resources/strategies/slatSmall Business Accounting Method Exemptions (Section 448(c))How one gross receipts test under Section 448(c) exempts a small business from accrual accounting, inventory rules, UNICAP and percentage of completion. Read more at https://timcpa.com/resources/strategies/small-business-cash-method-263aSocial Security Claiming Strategy (Section 86)How Section 86 decides what share of a Social Security benefit is taxed, why the claiming age does not change that, and what the earnings test counts. Read more at https://timcpa.com/resources/strategies/social-security-claiming-strategySolo 401(k)How a solo 401(k) lets a business owner contribute as both employee and employer, and why a single hidden hire can quietly disqualify the plan. Read more at https://timcpa.com/resources/strategies/solo-401kStartup and Organizational Costs (Sections 195, 248, 709)How Sections 195, 248 and 709 recover pre-opening costs, why each pool carries its own $5,000 cap, and why the date a business begins decides everything. Read more at https://timcpa.com/resources/strategies/startup-and-organizational-costsStep-Up in Basis Planning (Section 1014)How section 1014 resets an inherited asset's basis to its date-of-death value, wiping out capital gains and depreciation recapture built up during life. Read more at https://timcpa.com/resources/strategies/step-up-in-basis-planningTax-Loss Harvesting and the Wash-Sale Rule (Section 1091)How capital losses net under Section 1222, the $3,000 ordinary income cap, indefinite carryforward, and the wash-sale rule that quietly voids it. Read more at https://timcpa.com/resources/strategies/tax-loss-harvestingThe Trifecta (Trust, Operations, and Holding Entity)How the Trifecta puts a revocable living trust over a separate operating entity and a holding entity, what each leg actually does, and where it fails. Read more at https://timcpa.com/resources/strategies/the-trifectaThe UPREIT 721 Exchange (Section 721 Contribution)How contributing real estate to a REIT operating partnership under section 721 defers gain, why it is not a 1031 exchange, and what it costs permanently. Read more at https://timcpa.com/resources/strategies/upreit-721-exchangeVacation Homes and Mixed-Use Dwellings (Section 280A(d))How Section 280A(d) counts personal-use days, when a vacation home's deductions cap at rental income, and why the interest allocation is disputed. 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