Knowledge Library
Articles and practitioner guidance organized around this planning area.
Insight
Loss harvesting is not simply selling positions that are down. Wash sales, capital-loss carryovers, gains, portfolio objectives, state rules, and future transactions should be coordinated.
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Business and rental losses can be limited separately by basis, at-risk, passive activity, and other rules. Each limitation requires its own history and release event.
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Split-interest planning can coordinate charitable intent, appreciated assets, income streams, business sales, and estate objectives, but requires early timing, valuation, trust administration, assignment-of-income analysis, and specialist involvement.
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A profitable Schedule C can be a planning trigger. It is not, by itself, a reason to elect S corporation status. The analysis should integrate reasonable compensation, QBI, retirement plans, benefits, state tax, administration, financing, basis, and eventual exit.
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Basis drives gain, loss, distributions, depreciation, and loss limitations. The practitioner should preserve provenance and reconstruct missing basis before relying on inherited software numbers.
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Residency and source are separate questions. Work location, business activity, real property, stock compensation, installment sales, retirement income, credits, withholding, and local taxes can all change the result.
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Succession requires coordination of ownership, management, successor readiness, valuation, financing, tax structure, customer continuity, employee continuity, and the owner’s post-transition role.
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Reasonable compensation is a fact-based professional determination that should be supported, documented, and revisited as the shareholder’s role and the business change.
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Marketplace premium tax credit results can change with capital gains, Roth conversions, business income, self-employed health insurance, retirement contributions, household changes, and state coverage rules.
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State residency tests differ. Practitioners should identify every state that could assert residency, apply that state’s test, document the move, and separately analyze income that remains sourced to the former state.
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The practitioner should identify why value is needed, the valuation date and interest, distinguish enterprise from equity value, normalize earnings carefully, and use qualified valuation professionals when a formal appraisal is required.
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Qualification as a real estate professional does not automatically make rental losses nonpassive. Material participation, grouping, documentation, and the taxpayer’s actual activities still control the result.
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A net operating loss can affect multiple years. Origin, character, carryforward rules, state conformity, ownership changes, and future income should be preserved and modeled.
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A properly operated reimbursement process can move legitimate business expenses from the owner to the business without turning reimbursements into wages. Substance, substantiation, return of excess, entity type, and consistent operation matter.
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Buy-sell agreements coordinate triggers, valuation, funding, redemption or cross-purchase tax treatment, insurance, basis, estate consequences, and business continuity. Existing insured redemption arrangements deserve post-Connelly review.
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Roth conversions are most useful when modeled across several years and coordinated with RMDs, Social Security, Medicare IRMAA, ACA, capital gains, charitable planning, survivor taxation, state residence, and liquidity.
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The excess business loss limitation can defer an otherwise real business loss. The practitioner should separate current limitation, NOL consequences, basis, at-risk, passive activity, and state treatment.
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Fringe-benefit treatment depends on entity, ownership, employee status, nondiscrimination rules, payroll reporting, and the specific benefit. Owner status must be identified before the benefit is characterized.
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