Knowledge Library
Articles and practitioner guidance organized around this planning area.
Insight
A low-income year can create an opportunity to recognize gain deliberately, but the practitioner should model capital-gain brackets, NIIT, ACA, IRMAA, state tax, loss carryovers, and future basis.
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Estimated tax and withholding are cash-flow and penalty-management tools. Safe harbors, uneven income, payroll withholding, retirement distributions, state payments, and year-end flexibility should be coordinated.
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Year-end planning works best as a coordinated review of income, deductions, retirement, business activity, investments, healthcare, charitable giving, states, and implementation deadlines.
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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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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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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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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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Alternative minimum tax can still affect stock options, private activity bond interest, deductions, credits, and timing decisions. Planning should identify the items that move differently under the parallel system.
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Options, restricted stock, RSUs, ESPPs, and employer shares can produce different ordinary income, capital gain, AMT, withholding, basis, and concentration consequences.
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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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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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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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Marriage and divorce affect filing status, liability, dependents, property basis, retirement accounts, ACA, businesses, community property, carryovers, withholding, and professional-conflict issues.
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Filed tax returns should be retained permanently. Supporting records should be retained according to the life of the asset or tax attribute, applicable federal and state limitation periods, and any longer special or non-tax requirements.
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