Layered Capital Gains Case Study: Four Transactions

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.