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The Real Estate CPA Podcast Crash Course: Tax Deferral Strategies

Posted by Ben Isley on Jun 20, 2020

This Crash Course is designed to compile all of our podcasts episodes about tax deferral in an order that will cover the subjects from start to finish.

Working through these episodes in order will provide thorough education on these subjects. If you're interested in tax deferral strategies for real estate, you have come to the right place!

In this tax deferral series, we cover 1031 exchanges in depth from square one all the way through to the most advanced 1031 exchange strategies. We also cover Delaware Statutory Trusts, Deferred Sales Trusts, and installment sales.

All of the episode links below will direct you to the show notes where we look to move all of the important information spoken about on the episode to a written format.

1031 Exchanges

Episode 22: The Ins and Outs of 1031 Exchanges with Bill Exeter

This episode, Bill Exeter walks through everything related to forward 1031 exchanges, which are the traditional and most common form of this strategy. Successfully executing a 1031 exchange allows the investor to defer the capital gains tax and use the entire proceeds from the sale on a new investment property. Learn directly from Bill on how to successfully execute a 1031 exchange below.


Episode 100: How Reverse and Improvement 1031 Exchanges Can Offer Flexibility with Atlas 1031 Exchange

In the first episode with Bill Exeter we learn that forward 1031 exchanges involve selling a property and subsequently identifying a new property and closing within a specified timeframe.

In this episode with Tom and Andy Gustafson of Atlas 1031 Exchange, we learn about how to add some flexibility to that timeline with a reverse 1031 exchange and about more creative uses of sales proceeds with improvement 1031 exchanges.

Episode 56: How Combining 1031 Exchanges with Delaware Statutory Trusts Helps Defer Taxes and Grow Your Wealth with Jay McPherson

In this episode with Jay McPherson, we discuss Delaware Statutory Trusts used in combination with a 1031 exchange to defer capital gains tax and depreciation recapture tax. This strategy is most common where the investor would like to be done actively managing real estate or would like to move out of management and into a more diversified pool as a passive real estate investor.

Episode 101: Using 1031 Exchanges and 721 Exchanges (UPREITs) to Acquire Shares of a REIT with Warren Thomas

This strategy is advanced and involves multiple very important and totally separate steps. In this episode, Warren Thomas walks us through the process of 1) 1031 exchange 2) Delaware Statutory Trust and 3) Section 721 exchange.

Executing this strategy allows the investor to exchange the entire sales proceeds for shares of a Real Estate Investment Trust (REIT).

Episode 75: Everything You Need to Know About Drop and Swaps, a 1031 Exchange Strategy with Matt Rappaport

In this episode with Matt Rappaport, we discuss Drop and Swaps. This strategy applies to real estate deals with multiple investors. Executing a drop and swap allows each individual to do what he or she sees fit with the proceeds, including a 1031 exchange with their portion.


Check out this blog post: Pros and Cons of a 1031 Exchange

Deferred Sales Trusts and Installment Sales

Episode 62: Why Consider a Deferred Sales Trust When Selling Your Next Property with Greg Reese

First off, we discuss two types of DST's. Delaware Statutory Trusts and Deferred Sales Trusts. These are not the same. In this article, Greg Reese explains the differences.

In this episode, Greg focuses specifically on Deferred Sales Trusts, an alternative strategy that allows the investor to defer capital gains. This is a specialized form of an installment sale. With a Deferred Sales Trust, the investor is not executing a 1031 exchange or interacting with a Delaware Statutory Trust - this strategy involves selling the property directly to the Deferred Sales Trust.

Episode 103: How to Cash Out and Defer Capital Gains Tax Using Monetized Installment Sales with Ruth Benjamin

In this episode with Ruth Benjamin, we walk through the differences between traditional installment sales and monetized installment sale. An installment sale essentially allows the investor to defer capital gains by becoming the bank - capital gains are spread out over the life of the payments. When this loan is monetized, aka sold to a private lender through a capital asset dealer, the investor receives almost the entire sales price of the asset in the form of a loan, which is not a taxable event.

Clicking the episode links will take you to the post of the podcast episode where you can read much more in-depth show notes taken on the episodes.

For any real estate tax education you seek, check out our comprehensive guide:

The Ultimate Guide to Tax Planning for Landlords and Buy and Hold Investors

Topics: Crash Course

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