Beyond the 1031 Exchange: Real Estate Gains Deserve a Broader Planning Conversation

06/05/25 9:58 AM - By Sterling Hirsch

Not long ago, one of our advisor partners introduced me to a client preparing to close on a sizable real estate transaction. The sale itself was a financial win. The tax consequences were going to be significant. His regular income was modest, which meant this transaction would create a substantial spike in his taxable picture for the year.

As we reviewed the situation together, a familiar challenge surfaced - one I encounter often: the immediate assumption that a 1031 exchange is the only answer.

A 1031 Is a Powerful Tool. It's Not the Only One.

A 1031 exchange is often the right move for deferring capital gains on real estate, and in many cases it's smart. But when it's presented as the default - before anyone has taken a close look at the client's full situation - the conversation gets narrowed before it should.

For this client, we didn't start with "how do we execute a 1031. " We started with a different question: does a full exchange, a partial exchange, or some combination of strategies actually serve his long-term goals? Those are different questions, and they lead to different answers.

Objective Guidance Matters More Than Product Familiarity

There's a common dynamic in this industry worth naming directly. Some advisors - often with genuinely good intentions - tend to default toward investment portfolios structured around real estate: DSTs, REITs, or other managed vehicles.

These may be appropriate in certain situations. But too often, the recommendation reflects product familiarity or business structure more than a clear picture of what the client actually needs. That's not how we operate.

At Collective VFO, we don't sell investments. If a managed real estate solution becomes worth exploring, we connect clients with licensed financial advisors who specialize in those strategies - professionals we've vetted, who engage in transparent due diligence and present options with the client's objectives at the center.

The recommendation comes from analysis, not from what's on the shelf.

Tight Timelines Create Pressure - Unless You Plan Ahead

The 45-day identification window after closing is one of the most stress-producing elements of a 1031 exchange. If the client intends to roll gains into a property they'll manage themselves, and the right property isn't available, that window closes fast.

Having professional guidance and backup options in place before closing - not after - changes what's possible. It expands the conversation from "what's available right now" to "what actually fits. "

It's Rarely Either/Or

The most effective real estate planning outcomes usually come from layered strategies, not a single move.

A partial 1031 might make sense for one portion of the proceeds. A post-sale tax strategy might address another. The client's estate planning, income needs, or long-term goals might call for a different conversation altogether. That kind of layered thinking can't happen when an advisor is working in isolation.

Why Coordination Changes the Outcome

Most advisors operate independently of each other - making decisions without visibility into what the client's CPA, attorney, or other professionals are doing. That's where costly oversights happen. Not usually through bad advice, but through incomplete pictures.

At Collective VFO, we bring the right professionals to the table - including the client's existing advisors when possible - and ensure every strategy is built against the client's full financial situation. Not just the transaction in front of us.

Where Collective VFO Fits

What we coordinate: Real estate transaction planning across your CPA, financial advisor, and attorney - evaluating 1031 exchanges, partial strategies, and post-sale options against your full financial picture.
Who this is for: Real estate investors and business owners with significant transaction gains and planning needs - and the CPAs and advisors who work with them.

Next step: Start with a short conversation →

Collective VFO facilitates strategic coordination across tax, legal, and financial planning disciplines. We do not provide legal, accounting, securities, or investment advisory services directly. Any such services are provided by appropriately licensed professionals. The content in this article is for educational purposes and does not constitute financial, legal, or tax advice. For guidance specific to your situation, consult a licensed professional.

Ready to talk about what this means for your situation?

The first step is a short conversation. We review every inquiry personally and will tell you directly whether there's a fit.

Sterling Hirsch

Sterling Hirsch

Advanced Planning Lead Collective VFO

Sterling founded Collective VFO to address a gap in advisory work: business owners with good, but disconnected, individual advisors. He leads advanced planning for high-net-worth business owners/families, coordinating implementation with CPA partners across tax, legal, estate, and business planning.

Share -