Capital Gains Tax Planning

Layered Capital Gains Case Study: Four Transactions

A case-study briefing on why capital gains planning should start with income replacement, not just the tax bill.

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Featured visual for Layered Capital Gains Case Study: Four Transactions, a JPOPE Capital Gains Tax Planning case study resource

Planning resource

A working asset for the next advisor conversation.

Use this resource to organize the facts, records, and timing questions before the planning window narrows.

Format

Case Study

Window

Sell

Output

CPA-ready

Direct answer

Use this resource to organize the decision before deeper analysis starts.

Direct answer

A case-study briefing on why capital gains planning should start with income replacement, not just the tax bill.

Best planning window: Instead of treating the sale as a single tax event, the advisory team compared income replacement, partial exchange structure, family goals, charitable planning, and the buyer/seller chain created by the transaction.
Facts that change the answer: A full 1031 exchange is not the only disposition planning route. A partial exchange can preserve income while freeing capital for other objectives.
Expected output: Case Study context packaged for an owner and advisor next step.

Ask the CPA or advisorWhich capital gains tax planning facts still need verification before the current decision window closes?

Layered planning model

The best sale plan starts with the owner outcome, then layers the tax tools.

The doctor case is a strong JPOPE story because the first question was income replacement, not just tax reduction.

$19M

sale size

Disposition that could have stalled without planning.

$8M

income leg

Partial exchange used for replacement income.

transactions

Follow-on planning chain created by one structured sale.

Case chart

Sale proceeds routed by purpose

Bars use the public case amounts: $19 million sale proceeds, $8 million into replacement income, and $11 million left for other objectives.

Gross sale

Original disposition size.

$19M

Replacement property leg

Exchange portion tied to income replacement.

$8M

Other owner objectives

Capital available for other planning goals.

$11M

Transaction chain

Follow-on opportunities from coordinated planning.

4 deals

Planning path

Step 1
Ask about replacement income
Step 2
Split the sale by objective
Step 3
Coordinate CPA and counsel
Step 4
Package the next transaction

Case StudySellownerinvestorbrokeradvisorCPA

Last updated: 2026-06-30

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The first question was not tax

An owner considering a $19 million sale had a major capital gains problem, but Jamie's chapter frames the more important first question: how will the owner replace the income the property was producing?

That question changed the planning conversation. Instead of treating the sale as a single tax event, the advisory team compared income replacement, partial exchange structure, family goals, charitable planning, and the buyer/seller chain created by the transaction.

What the case teaches

A full 1031 exchange is not the only disposition planning route.
A partial exchange can preserve income while freeing capital for other objectives.
One well-planned transaction can create follow-on opportunities for other owners.
Brokers can unlock more transactions when the tax problem is framed early.
CPA, attorney, broker, and specialist coordination matters more than any single tactic.

Planning checks

What income disappears after the sale?
Which portion of proceeds must remain invested in real estate?
Which portion is needed for family, estate, charitable, or liquidity goals?
Does the replacement property make investment sense without tax pressure?
What does legal counsel need to structure before terms become fixed?

JPOPE planning lens

Capital gains planning should not start with "what shelter can we use?" It should start with the owner's next chapter, then build a compliant tax path around that reality.