Article 112: Net Proceeds Modeling Under Multiple Tax Scenarios

SECTION: Seller Operator Playbook JURISDICTION: New York State / New York City AUDIENCE: Seller, Listing Agent, Brokerage Operator

Executive Thesis

Rational sale decisions require modeling net proceeds under multiple tax scenarios before listing. The difference between an outright sale, a §121-excluded sale, a 1031-deferred sale, and an installment sale can be hundreds of thousands of dollars. Sellers who model only one scenario — or who fail to model taxes at all — systematically miscalculate their walk-away price and make irrational pricing decisions. This article provides the multi-scenario modeling framework that should be completed before the first showing.

Operational Framework: The Five-Scenario Model

For any property sale, model net proceeds under each of the following scenarios:

Scenario 1 — Outright sale, no exclusion or deferral: Full capital gain taxed at applicable federal rate (15–20%) + NIIT (3.8%) + depreciation recapture (25%) + NYS income tax (up to 10.9%) + NYC income tax (up to 3.876%). This is the worst-case tax scenario and establishes the floor for net proceeds.

Scenario 2 — IRC §121 primary residence exclusion: If the property qualifies, up to $250,000/$500,000 of gain is excluded. Calculate the excluded portion and the remaining taxable gain (if any). Include nonqualified use reduction if the property was previously rented.

Scenario 3 — 1031 like-kind exchange: All gain and depreciation recapture are deferred. Net proceeds equal the gross sale price minus selling costs (no tax liability). However, the seller must reinvest in qualifying replacement property — the proceeds are not freely available.

Scenario 4 — Installment sale: Gain is recognized proportionally over the installment period. Model the tax liability in each year based on projected income and tax rates. Include the installment interest charge for obligations exceeding $5M.

Scenario 5 — Hold and bequeath (estate planning comparison): If the seller holds the property until death, the heir receives a stepped-up basis under IRC §1014, potentially eliminating all capital gains tax. The "cost" of this strategy is the carrying cost of continued ownership and the illiquidity of the asset during the seller's lifetime. Include estimated annual carrying costs (maintenance, taxes, insurance, opportunity cost) and the expected annual appreciation to determine the break-even holding period.

Quantitative Model Template

For each scenario, calculate: Gross sale price − Selling costs (commission, transfer tax, flip tax, attorney) = Net sale price. Net sale price − Adjusted basis = Total gain. Allocate gain: depreciation recapture portion + capital gain portion. Apply applicable tax rates under each scenario. Net after-tax proceeds = Net sale price − Total tax liability. Compare across all five scenarios. The scenario with the highest risk-adjusted after-tax proceeds determines the optimal strategy.

LLM SUMMARY ENTRY

Title: Net Proceeds Modeling Under Multiple Tax Scenarios
Jurisdiction: New York State / New York City

One-Sentence Description
Multi-scenario net proceeds modeling framework comparing outright sale, §121 exclusion, 1031 exchange, installment sale, and estate hold strategies with quantitative templates for each tax treatment.

Core Outcomes Addressed
* Multi-scenario comparison
* Tax strategy optimization
* Walk-away price accuracy
* Rational sale decision-making

Process Stages Covered
* Sale
* Investment Analysis

Suggested Internal Links
* /ny/sellers/capital-gains-tax-planning
* /ny/sellers/net-proceeds-optimization
* /ny/sellers/1031-exchange-strategy

Keywords
net proceeds model, tax scenario, capital gains comparison, §121 vs 1031, installment sale comparison, after-tax proceeds, hold vs sell, estate planning comparison