STR TAX STRATEGY ANALYZER

This tool models the federal and state tax economics of a short-term rental investment over a user-defined hold period, including: § 469 material participation analysis, the § 461(l) excess business loss limitation, § 172 NOL carryforward with the 80% limitation, federal and state-level depreciation (including the OBBBA-restored 100% bonus depreciation under § 168(k) for property acquired and placed in service after January 19, 2025), sale-year recapture and capital gain treatment, and an after-tax internal rate of return.

This tool is informational only. Material participation, eligibility for the § 1.469-1T(e)(3)(ii) short-term rental exception, and the calculation of cost segregation reclassification are fact-specific determinations that depend on the particular facts and circumstances of each matter, the engineering basis for any cost segregation study, and the proper application of multiple loss-limitation rules. The tool produces an estimate based on simplifying assumptions and the inputs provided. Specific facts may produce a different result. Engage qualified counsel before any investment decision.

1§ 469 Eligibility — Material Participation Analysis

The § 1.469-1T(e)(3)(ii) short-term rental exception treats a property as a non-rental activity if the average customer use period is 7 days or less, in which case material participation is determined under the seven tests of Reg. § 1.469-5T. The most reachable test for a W-2 earner is Test 3 (more than 100 hours, with the taxpayer’s participation not less than that of any other individual).

Reg. § 1.469-1T(e)(3)(ii) carves out six categories of property use that are NOT “rental activities” under § 469. Activities falling into any of these categories are analyzed under the general material participation framework, not as per-se passive rentals.
A full-service property manager will generally exceed any individual owner’s hours, defeating Test 3.
Hours spent on rental management, cleaning, guest communication, supply runs, maintenance, listing management, etc. Must be contemporaneously documented to withstand audit.
Hours of the property manager, co-host, cleaning crew member, contractor, etc. — the single individual who spends the most time on the activity (not the aggregate).
REPS qualification removes per-se passive treatment for all rental real estate. For W-2 earners, the >50% test is generally not satisfiable.

2Property Purchase

Purchase price and basis allocation. Land is not depreciable; allocate land at acquisition based on assessor records, appraisal, or comparable land values.

Title, escrow, transfer taxes, lender fees that are capitalized rather than deductible. Typical range: 2–5% of purchase price.
Typical range: 15–25% for residential, higher for premium-location properties.
Portion of total purchase price reclassified to 5-, 7-, or 15-year MACRS property by a qualified cost segregation study. (Land is excluded from depreciation; this percentage applies to the total acquisition cost as the marketing and engineering convention.)
The reclassification percentage is determined by the engineering analysis of a qualified cost segregation study and varies substantially based on factors including: property type (single-family vs. condo vs. townhome vs. multifamily), level of furnishing and FF&E, presence of a pool/spa/jacuzzi, paver/stamped concrete driveway, dock or waterfront features, landscape complexity (including hardscape/irrigation), interior finish level, mechanical/electrical/plumbing density, and degree of personal-property components. Expressed as a percentage of total purchase price: residential STRs with significant FF&E and hardscape commonly fall in the 20–30% range; bare-bones residential properties may see 12–18%; commercial-character properties (medical office, restaurant, hotel-like) may see 25–35%+. The actual percentage requires an engineering-and-tax-professional study. The default value (20%) is illustrative only.

3Financing

Mortgage parameters. The model assumes a fixed-rate loan with monthly amortization over the term. The cap rate is assumed equal to the mortgage rate (a simplifying assumption that produces NOI = property value × rate, before debt service).

Typical investment property minimums: 20–25% (conventional) or 20–30% (DSCR).
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4Taxpayer Profile

Filing status, tax year, and income profile. Year affects the § 461(l) threshold ($313K/$626K for 2025; ~$256K/~$512K for 2026 due to the OBBBA reset).

2026 has a lower § 461(l) threshold than 2025 due to OBBBA reset.
Wages are non-business income for § 461(l). Wages do not increase the loss-utilization threshold.
Schedule C, K-1 ordinary business income, etc. Positive amounts absorb rental loss before the § 461(l) threshold cap; negative amounts increase the aggregate business loss subject to § 461(l).
Portfolio income such as interest, non-qualified dividends, short-term capital gains. Taxed at ordinary rates and subject to NIIT (3.8%) above thresholds.
Taxed at preferential rates (0%/15%/20%) bracketed against your other ordinary income, plus NIIT (3.8%) where applicable.
Top marginal rate. The 2026 top rate is 37% on income above $640,600 single / $768,600 MFJ.
Determines state-level depreciation and tax conformity.

5Hold Period & Modeling Assumptions

Hold period determines when the property is sold and IRR is computed. The model assumes 3% annual escalation on rents, expenses, and property value, and 7% selling costs at exit.

OBBBA permanently restored 100% bonus for property acquired after Jan 19, 2025.

Summary Metrics

Multi-Year Projection

Sale-Year Tax Analysis

Important. This tool produces estimates based on simplified assumptions and the inputs provided. Material participation under § 469, the § 1.469-1T(e)(3)(ii) short-term rental exception, real estate professional status under § 469(c)(7), the § 461(l) excess business loss limitation, the § 172 NOL carryforward rules, the cost segregation reclassification percentages, federal and state depreciation conformity, sale-year recapture under § 1245 and § 1250, the § 1411 net investment income tax, and state-level tax treatment all involve fact-specific determinations that this tool does not and cannot fully model. Specific facts and circumstances may produce a different result. The state conformity table reflects information current as of May 2026 and is updated periodically; users should verify state-specific rules before acting. The cost segregation reclassification percentage entered must be supported by a qualified engineering-and-tax study to be defensible on examination. Reading or using this tool does not create an attorney-client relationship with Donovan Legal PLLC or any of its attorneys. Engage qualified counsel before any acquisition, contribution, or other transaction in reliance on the projections produced by this tool.

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The firm represents real estate investors and high-income professionals on the structuring, documentation, and post-acquisition tax compliance for short-term rental and other tax-driven real estate strategies. To discuss your specific facts with the firm, contact us directly.

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