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In this episode, Tim Vi Tran, SIOR, CCIM, breaks down how different types of boot—cash, debt relief, and non–like-kind property—are taxed, why depreciation recapture and capital gains are treated differently, and how the order of taxation affects what you keep in your pocket. You’ll hear practical scenarios for Bay Area commercial real estate owners, when to avoid boot to maximize deferral, when taking boot can improve portfolio fit or liquidity, and a simple “2/3 rule of thumb” for estimating after-tax cash. We’ll also walk through a pre-, during-, and post-exchange checklist so you can better coordinate with your qualified intermediary, CPA, and legal team.
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About The Ivy Group
The Ivy Group specializes in commercial sales, leasing, and investment advisory across Fremont, Silicon Valley, and the Greater Bay Area
For a small fee, you can access this case study in full at: 👉https://theivygroup.com/course-category/cre-strategies-tactics/
When commercial property owners ask, “Should I sell or lease?” They’re rarely just talking about numbers. They’re really asking, “What do I want my next 5–10 years of life to look like?”
This case study is about a Fremont owner who faced exactly that crossroads with a tech/flex building in Fremont’s Warm Springs Innovation District in California. On paper, he had options: 1) sell and pay a substantial capital gains tax bill; 2) complete a 1031 Exchange into another property; 3) invest the sales proceeds into a Delaware Statutory Trust for passive income, or; 4) keep the property and simply lease it for rental income.
He trusted that The Ivy Group would advise him from the standpoint of what’s in his best interest, proven from a prior representation where we walked with him through a different challenge: securing a long-term lease for a daycare in a highly regulated, supply-constrained Bay Area market. By solving zoning, permitting, and timing hurdles, and negotiating terms that supported over $1 million in tenant improvements, we built a relationship grounded in execution and trust. That experience set the stage for a much bigger decision on this Fremont property.
We laid out a four-column matrix —Sell, 1031, DST, Hold & Lease—so he could compare cash flow, tax exposure, and lifestyle implications side by side, instead of pushing a sale or a 1031 exchange.
To find out exactly why the owner chose a “hold and lease” strategy, how The Ivy Group secured two high-quality tenants over eight years, and what process we used to keep vacancy to essentially zero, for a small fee, you can access this case study in full at: 👉https://theivygroup.com/course-category/cre-strategies-tactics/
👉 Subscribe to The Ivy Group newsletter: https://theivygroup.substack.com/
📩 Contact The Ivy Group: https://theivygroup.com/contact-us/
If you own commercial property and are wrestling with whether to sell, exchange, or keep collecting rent, this story offers a different lens: start with your life, then use the tax code as a tool—rather than the driver of your decisions.
The Ivy Group. Commercial Properties. Above and Beyond.
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