Most investors don't think about tax strategy until the day they list a property, but by then, the best options could be off the table. In this episode of The Exchange Brothers, David and Tom Moore break down why tax planning needs to start at acquisition, not disposition, and unpack two of the most misunderstood tools in a 1031 investor's toolkit: TIC and DST ownership structures, and mixed-use property conversions.

0:00 Welcome back, and the "no second-home changes" myth 

3:34 Why planning is the whole game 

6:57 Do you actually have a tax liability?

10:25 Facilitator vs. accommodator (and blending 1031 with IRA money) 

13:24 Reddit case: a rental into a new primary home? 

18:39 Converting a 1031 into a residence — why the "genius" move fails 

33:46 "Exchange or sell," ADUs, and hold-period myths 

43:25 Forever homes, the 121 exclusion debate, and vesting traps 

57:25 TIC vs. DST, diversification, and the $500K deferral-cap threat 

You can find every episode of this show on Apple Podcasts, Spotify or YouTube. For more, visit 1031exchange.com 

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Before the mics were officially on, Jose Cienfuegos of Revitalize Portland Coalition got real about what's actually happening in Portland right now. 

Oregon left federal tax incentives on the table. DA budgets are getting slashed. The Blazers stadium question is reshaping Portland's national profile. And inside City Council, things look very different up close than they do in the headlines.

But here's the twist — Jose sees a come-together moment forming. The doom loop narrative isn't the whole story anymore.

This is the unscripted conversation that set the table for everything in the full episode. 

Topics: Portland's enforcement priorities | Oregon tax policy | City Council from the inside | DA budget cuts | The Blazers & Portland's future

🎙️ Full episode available now on The Exchange Brothers. 

📞 1031 exchange questions? Call Equity Advantage: 503-635-1031 

🌐 1031exchange.com

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Portland is at a turning point, and the people watching closest say the window to act is now. David Moore sits down with Jose Cienfuegos, president of the Revitalize Portland Coalition (10,000 members, 25 companies invested in the city's comeback), to talk about what's actually changing on the ground: distressed buildings trading at resets that finally pencil, a new executive mayor asking for a wish list of code changes, prosecution and livability enforcement returning, and major players like Swickard and Schnitzer doubling down on downtown. 

Jose — a former public defender and prosecutor who never planned on real estate — explains why he believes "this is the five years ago" moment investors always wish they'd caught, what still needs fixing, and how out-of-state investors can dictate their terms to a city that's finally listening.

Learn more about the Revitalize Portland Coalition at https://www.revitalizeportland.com/.

Chapters:

1:30 – From public defender to RPC president
4:50 – What is the Revitalize Portland Coalition?
6:28 – The state of the market: rent control refugees & phantom gains
10:17 – Portland's permanent assets & the confidence comeback
16:28 – Distressed buildings & "this is the five years ago"
28:01 – Summer birds: Schnitzer's vision for remaking downtown
41:28 – Permitting reform & the mayor's code wish list
1:10:05 – Investor advice: Big Pink at $40M & getting in early

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Intro (00:00). What is a reverse 1031 exchange and why it matters when you find the perfect property before you've sold your old one (00:58). The two reverse exchange structures — parking the replacement property vs. parking the relinquished property (04:49). The Exchange Accommodation Titleholder (EAT) explained (05:43). How the money and financing works in a reverse (06:55). Step-by-step walkthrough with a real example (09:04). Safe harbor vs. non-safe harbor transactions and why the cost difference is significant (14:52). Biggest risks and how to avoid them (16:07).

Ready to start your reverse exchange? Equity Advantage has facilitated 1031 exchanges since 1991. Call us at 503-635-1031 or visit 1031exchange.com.

You can find every episode of this show on Apple Podcasts, Spotify or YouTube. 

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1031 + IRA + Airbnb + Reverse Exchanges Overview (00:26). Market Changes & New Tax Legislation (02:13). Can You Combine a 1031 Exchange with a Self-Directed IRA? (08:16). Deal Structuring: Ownership, Loans & Key 1031 Rules (10:20). UBIT Explained (13:48). Advanced Strategy: Owning Property in an IRA Long-Term (19:34). Airbnb & Short-Term Rentals: Do They Qualify for 1031? (38:36). IRS Vacation Home Rules (Rental vs Personal Use) (42:36). IRA Deal Mistakes That Trigger Massive Taxes (Real Case Study) (50:01).  

You can find every episode of this show on Apple Podcasts, Spotify or YouTube. For more, visit https://www.1031exchange.com/podcasts/

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1:19 — F1 Experience & Japan Sabbatical
7:14 — The Bear Encounter
11:14 — Mentorship & Entrepreneurship
15:30 — From Flipping Houses at 19 → Property Management
18:36 — Oregon Rent Control & Market Reality
24:28 — Investor Strategy & Property Management Insights

Nick Cook started flipping houses at just 19 years old—during the height of the NINJA loan era. Today, he leads one of Oregon’s top property management companies and helps real estate investors navigate one of the most complex rental markets in the country.

In this episode, David Moore sits down with Nick Cook of SleepSound Property Management to break down Oregon’s statewide rent control law, what it actually means for landlords, and how investors should be thinking about Portland real estate today.

We also cover:

• Why rent control can lead to higher rents over time
• What most property managers don’t tell owners
• How to evaluate Portland as a long-term vs. short-term investment
• The biggest mistakes landlords make (and how to avoid them)
• Nick’s journey from flipping houses at 19 to building a successful company

Whether you're a real estate investor, landlord, or considering a 1031 exchange, this episode offers practical insights you can apply immediately.

About Equity Advantage

Equity Advantage specializes in 1031 exchanges, helping investors defer capital gains taxes and build long-term wealth through real estate.

👉 Learn more: https://www.1031exchange.com/
📞 Contact us: 503-635-1031

You can find every episode of this show on Apple Podcasts, Spotify or YouTube. 

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00:00 Intro: Flipping Properties with an IRA
01:03 Prohibited Transactions & IRS Risks
02:13 UBIT Tax: Why Flips Get Taxed
03:24 Investor vs Dealer Status Explained
05:22 Sweat Equity & Legal Ways to Flip (ROBS Option)

Thinking a Roth IRA flip means zero taxes? Not so fast. Most investors get this wrong… and the IRS has no sense of humor when they do.

In this episode, Dave and Tom Moore from IRA Advantage break down exactly what happens when you try to flip properties inside a self-directed IRA or 401K, including the rules that can blow up your entire retirement account if you cross the wrong line.

The bottom line: Self-directed IRAs are powerful tools for real estate investors, but only if you know where the lines are. This episode gives you the map.

Disclaimer: All my opinions are my own. These statements are not meant to be taken as investment advice.

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00:00 – The BIG Myth: Do You Have to Replace Debt in a 1031?
04:24 – How to Pull Cash Out Without Triggering Taxes
04:43 – Cash-Out Refi Timing: What Triggers IRS Problems
05:09 – The “Step Transaction” Rule (What Can Get You Audited)
09:40 – Costly Mistake: Over-Financing & Unexpected Taxes

Many investors are told they have to replace debt in a 1031 exchange, but that’s not always the case. In this episode, we walk through how debt can be offset, when taking cash can trigger taxes, and how to structure transactions the right way.

We also dive into one of the biggest risk areas: timing. A cash-out refinance done too close to a sale or acquisition can raise red flags with the IRS under the “step transaction” doctrine.

You’ll learn when a refinance makes sense, how intent factors into the equation, and why what you do with the money matters just as much as when you take it.

If you’re looking to access equity while preserving your tax deferral, this episode will help you understand the rules and avoid costly mistakes.

You can find every episode of this show on Apple Podcasts, Spotify or YouTube. For more, visit https://www.1031exchange.com/podcasts/

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In this episode, we break down one of the most misunderstood parts of a 1031 exchange: the identification rules.

Many investors know about the 45-day identification deadline, but far fewer understand how the three identification rules actually work or how mistakes during identification can jeopardize an exchange.

We discuss the fundamentals of identifying replacement property, common misunderstandings, and how identification works when investors are acquiring multiple properties, DST investments, or partial ownership interests.

If you're planning a 1031 exchange, understanding the identification process can help you avoid costly mistakes and structure your exchange more effectively.

Episode Timestamps

00:00 Introduction
05:19 Why Identification Confuses Investors
06:02 The 45-Day and 180-Day Deadlines
09:17 Who Receives Your Identification
11:12 How to Properly Identify Replacement Property
19:15 The 3 Identification Rules Explained
26:11 Why You Shouldn't Rush Identification
33:11 Combining Multiple Properties in a 1031 Exchange
41:48 Taking Cash Out of a 1031 Exchange

You can find every episode of this show on Apple Podcasts, Spotify or YouTube. Prime Members can listen ad-free on Amazon Music. For more, visit https://www.1031exchange.com/podcasts/ 

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00:00 – Reddit Question: 1031 Exchange into a DST. 02:32 – DST vs 721 (UPREIT) Explained. 05:51 – 45-Day Rule Warning: DON'T LET IT CLOSE. 07:53 – Sponsor Risk & Why Experience Matters. 09:56 – How 721 Lets You Sell Through Basis. 14:43 – DST Identification Rules & Common Mistakes. 20:02 – Final Thoughts: “What Good Is Tax Deferral If What You Buy Goes Away?”

You can find every episode of this show on Apple Podcasts, Spotify or YouTube. For more, visit https://www.1031exchange.com/podcasts/

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