Capital Gains Tax Planning

1031 Exchange Rescue, QI, and DST Checklist

A sale-timing checklist for owners comparing 45-day identification pressure, qualified intermediary risk, DST options, and Opportunity Zone backup paths.

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

Checklist

Window

Sell

Output

CPA-ready

Exchange pressure model

The deadline is real, but it should not choose the investment for the owner.

The chapter reinforces a JPOPE principle: protect the exchange timeline, vet the intermediary, and keep backup paths visible before a failed deal turns into a tax panic.

45 days

identify by

Replacement property identification pressure point.

180 days

outer window

Acquisition or backup planning deadline to monitor.

before funds move

QI review

Service agreement terms can matter if the exchange fails.

Case chart

Timeline pressure points

Bars show the practical planning windows owners should track: Day 45 identification, possible QI return delay, and the 180-day outside window.

Identification window

Replacement property must be identified.

Day 45

Possible return delay

A contract term can affect backup timing.

90-day clause

Outside planning window

Monitor exchange and backup deadlines together.

Day 180

Planning path

Step 1
Vet QI terms
Step 2
Pre-screen replacement assets
Step 3
Model DST on investment merit
Step 4
Keep backup timing visible

ChecklistSellownerinvestoradvisorCPA

Last updated: 2026-06-30

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Why this checklist exists

A 1031 exchange can be powerful, but the deadline pressure can make owners buy the wrong asset, choose the wrong intermediary, or miss a backup strategy. The planning question is not only whether the exchange can work. It is whether the exchange still makes business sense.

Day-zero controls

Sale proceeds should move directly through the qualified intermediary process
Replacement property search should begin before the listing decision when possible
The advisor team should know who is tracking Day 45 and Day 180
The owner should understand what happens if an identified deal falls apart

Qualified intermediary review

Is the QI bonded and insured?
Are funds held in segregated accounts rather than commingled accounts?
What does the agreement say about returning funds after a failed exchange?
Who controls disbursement timing, and how quickly can funds be returned?
Has tax counsel reviewed the service agreement before money moves?

DST and backup questions

Is a DST being evaluated as an investment, not merely as a tax rescue?
Are sponsor fees, acquisition price, cash yield, exit plan, and liquidity clear?
Is the offering building-specific or a pooled fund with older assets?
If the traditional exchange fails, does an Opportunity Zone review still fit inside the original sale timeline?

JPOPE planning lens

The tax structure should serve the investment plan. If the only reason to buy the replacement asset is deadline pressure, the owner needs a second conversation before the tax tail starts steering the deal.