Ten chapters, in reading order.
Start at the beginning or enter at the decision in front of you. Each chapter opens with a plain-English summary and carries the practitioner detail one toggle away.
Foundation
Where the SIS came from, how it is built, and the installment-method rules it relies on.
History & Origins of the SIS
From thalidomide-era structured settlements to a modern capital-gains tool: the legal and market history of the Structured Installment Sale.
Read chapter → Plain · PractitionerChapter 2How an SIS Works
The mechanics of a Structured Installment Sale: parties, contracts, the non-qualified assignment, and the flow of funds.
Read chapter → Plain · PractitionerChapter 3The Tax Framework: IRC §453 in Depth
IRC §453, §453A, and §453B — the installment-method rules that govern Structured Installment Sale taxation.
Read chapter → Plain · PractitionerThe Structure
The substitution question at the center of every SIS, the assets it fits, and how it compares to the alternatives.
The Substitute-Obligor Question
How to analyze substitution, payment rights, §453B, and the limits of analogous authority.
Read chapter → Plain · PractitionerChapter 5Use Cases by Asset Type
How the SIS applies to real estate, business sales, farms, professional practices, and other capital assets.
Read chapter → Plain · PractitionerChapter 6SIS vs. Other Deferral Strategies
Comparing the Structured Installment Sale to §1031 exchanges, Opportunity Zones, CRTs, DSTs, and monetized installment sales.
Read chapter → Plain · PractitionerRegulation & Safety
Who regulates the parties, how payments are protected, and what a guaranty association does and does not cover.
Regulatory Framework
Federal and state regulation governing the SIS: IRS, Treasury, state insurance departments, and the NAIC.
Read chapter → Plain · PractitionerChapter 8Safety & Security of the SIS
Carrier solvency, statutory reserves, state guaranty associations, and how SIS payments are protected.
Read chapter → Plain · PractitionerEvaluation & Implementation
An honest weighing of the trade-offs, then the closing checklist.
Pros, Cons & Risk Analysis
Honest analysis of the SIS: its strengths, its trade-offs, and the situations where it does and doesn't fit.
Read chapter → Plain · PractitionerChapter 10Implementation Checklist / Setup Guide
Step-by-step implementation of a Structured Installment Sale: timing, parties, documents, and closing mechanics.
Read chapter → Plain · PractitionerContinue into the Deep Dives.
Fifteen question-driven articles on allocation and character, parties and entities, timing and cost of tax, and protection and geography.