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.

Send us Fan Mail

Thanks for listening! Subscribe to get all of the latest tax news and information.

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.

Send us Fan Mail

Thanks for listening! Subscribe to get all of the latest tax news and information.

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/

Send us Fan Mail

Thanks for listening! Subscribe to get all of the latest tax news and information.