Capital Gains Tax Planning

Tax Planning Case Study: $40 Million Portfolio

A case-study briefing on how early planning can change the economics of a large real estate disposition.

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

Disposition exposure map

A large sale needs the tax path modeled before the listing controls the answer.

The value is not a single tactic. It is getting gain, exchange practicality, basis, debt, timing, and family goals into one advisor conversation before sale terms lock in.

$40M

portfolio decision

Disposition size that can change owner behavior.

planning inputs

Gain, 1031 fit, basis, timing, and family goals.

advisor lanes

Owner, CPA, attorney, and real estate team.

Case chart

Decision file coverage

This case is strongest as a process chart because the public facts describe the decision architecture, not a final savings amount.

Planning path

Step 1
Estimate gain exposure
Step 2
Test 1031 practicality
Step 3
Map basis and entity constraints
Step 4
Compare after-tax exit paths

Case StudySellownerinvestoradvisor

Last updated: 2026-06-12

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Why this case matters

Large real estate dispositions can create tax exposure significant enough to change whether an owner wants to sell. The useful planning pattern is simple: review the tax issue before the owner assumes the sale is blocked.

Planning facts to organize

Estimated gain and likely tax exposure
Whether a 1031 exchange is practical in the current market
Ownership structure, basis, debt, and entity-level constraints
Timeline for listing, closing, reinvestment, and advisor review
Estate, succession, and family wealth goals that may affect the exit

Advisor conversation

The owner, CPA, attorney, and real estate team should understand the same options before a sale decision becomes difficult to change. JPOPE's role is to frame the tax problem, surface compliant alternatives, and package the analysis so the advisory team can evaluate the next move.