Anderson Business Advisors Podcast

How the IRS Is Using AI to Audit Cost Segregation Studies

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Is the IRS using artificial intelligence to audit cost segregation studies and real estate investors? Toby Mathis sits down with Chris Streit of CSA Partners to explain how AI is changing IRS audits, why cost segregation studies are receiving increased scrutiny, and what real estate investors should know before claiming large bonus depreciation deductions.

If you've already completed a cost segregation study—or you're considering one—understanding what the IRS looks for is increasingly important. This discussion covers how AI may help the IRS identify potential audit targets, what documentation auditors may request, and why some low-cost cost segregation studies may not withstand IRS scrutiny.

You'll also learn about common cost segregation mistakes that can increase audit risk, how to evaluate the quality of an existing study, and what you can do if you're concerned about a cost segregation report you've already received.

Learn more about CSA Partners 👉 https://csap.com/

How Cost Segregation Creates Large Real Estate Tax Deductions

Cost segregation can allow real estate investors to accelerate depreciation by identifying building components that qualify for shorter depreciation schedules. When combined with bonus depreciation, a cost segregation study can potentially create significant upfront tax deductions.

However, large deductions can also attract additional scrutiny. Investors should understand how their study was prepared, whether the classifications are properly supported, and what documentation is available if the IRS questions the deduction.

Why the IRS Is Increasing Scrutiny of Cost Segregation Studies

Cost segregation has become increasingly popular among real estate investors looking to maximize depreciation deductions. But not every cost segregation report is prepared to the same standard.

Toby and Chris discuss why the IRS may scrutinize aggressive depreciation claims and what separates a well-supported cost segregation study from one that could create problems during an examination.

The goal shouldn't simply be to generate the biggest tax deduction possible. The deduction should also be supported by a properly prepared and defensible cost segregation study.

Questions to Ask Before Hiring a Cost Segregation Firm

Before moving forward with a provider, ask questions about its experience, methodology, documentation, and support.

Understanding exactly what you're paying for can help you compare providers based on the quality of their work rather than simply choosing the cheapest cost segregation study or the company promising the largest deduction.

Get a Free Cost Segregation Benefit Analysis

Not sure whether cost segregation makes sense for your property?

Request a FREE Cost Segregation Benefit Analysis 👉 https://aba.link/154828

A benefit analysis can help you better understand the potential tax savings before deciding whether to move forward with a full cost segregation study.

Watch Next: Learn More About Cost Segregation

How To Do A Cost Segregation Study: When It Saves You Money And When It Doesn’t

Watch here 👉 https://youtu.be/beMOZDrXOJ8

Would you like to learn more about protecting your assets and minimizing taxes?

Schedule a FREE strategy session 👉 https://aba.link/tv5r

Chapters

0:00 – Intro
2:12 – How Cost Segregation Creates Large Tax Deductions
3:48 – Why the IRS Is Cracking Down
4:11 – The AI Technology the IRS Is Using
5:40 – How AI Flags Tax Returns for Audit
7:20 – How Often Are Cost Segregation Studies Audited?
8:11 – What IRS Auditors Ask For First
9:33 – The Risk of Cheap Cost Segregation Studies
10:28 – Can You Fix a Bad Cost Segregation Study?
12:48 – Can the IRS Target Specific Cost Seg Firms?
14:17 – What Should You Do If You're Concerned?
16:20 – How to Evaluate an Existing Cost Segregation Study
17:27 – Common Mistakes That Cost Investors Money
18:57 – How to Choose the Right Cost Segregation Company
20:38 – Questions Every Investor Should Ask Before Hiring a Firm
21:45 – Free Cost Segregation Analysis & Final Thoughts

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Have tax questions? Join us every other Tax Tuesday, where our tax professionals answer questions live—completely FREE.

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🔔 Subscribe for more insights on real estate investing, cost segregation, tax planning, asset protection, and business strategies.

In this Tax Tuesday replay, Anderson Business Advisors’ Barley Bowler, CPA, and Eliot Thomas, Esq. answer real-world tax questions on Roth IRA conversions, investing in real estate with retirement accounts, and depreciation after a 1031 exchange.

How can you estimate the tax impact of a Roth IRA conversion before filing your 2026 tax return? Is buying real estate through an HSA, traditional IRA, or Roth IRA a smart investment strategy—and what tax rules, advantages, and potential pitfalls should you understand before moving forward? Plus, how is depreciation calculated after a §1031 exchange when you sell a rental property and acquire a replacement property?

Barley and Eliot break down these questions and explain the tax considerations investors and business owners should keep in mind when planning their next move.

 

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Register for an upcoming workshop today if you want to protect your business and personal assets from snoopy lawyers and creditors. Save Your Seat: https://aba.link/7c2c4d 

 

Show Notes:

0:00 Intro

9:05 When I convert a Roth IRA this year how do I determine the accurate tax impact from the conversion amount before filing the 2026 tax return?

20:18 Is it a good idea to buy real estate using your HSA, IRA, or Roth IRA accounts? What are some pros and cons and how should I proceed?

35:51 How is depreciation calculated going forward after a §1031 exchange following the sale of a rental property and purchase of a new one?

43:41 I am planning to use a HELOC from my personal residence and use the funds for my trading activity. Can I deduct the interest as investment interest under Form 4952 if I loan the money to my LLC, and what counts as "net investment income"?

1:04:05 I will have a tax loss carryforward if I elect to use Section 475(f) mark-to-market accounting method. What types of income can I offset?

1:08:51 I currently have a Living Trust that ABA set up in Wyoming, as well as an LLC. I put all my cryptocurrencies into the LLC. Is this the best way to mitigate my taxes? I paid about $2.00 per share and the value is growing substantially. What other options might be better than the LLC?

1:12:42 Is there a way to organize and structure an entity to trade a taxable account and be able to defer taxes until a cash withdrawal?

What are the biggest Social Security and retirement mistakes retirees make? Toby Mathis and Erin Moriarity break down when to claim Social Security, Social Security taxes, Roth conversions, Medicare and IRMAA surcharges, the 4% rule, retirement income strategies, long-term care costs, and how to avoid running out of money in retirement. 

Learn how smarter Social Security planning, Medicare planning, tax strategies, and retirement withdrawal decisions can help you build a more secure retirement. 

Check out Erin's Channel 👇
https://www.youtube.com/@ErinTalksMoney 

Medicare Resource Mentioned in This Video: https://askchapter.org/ 

Many people do not realize how much of their social security benefits may be taxable until it is too late. 

By identifying these frequent social security taxes issues early, you can adjust your strategy to keep more of your money. This discussion is designed for anyone approaching retirement age who wants to avoid costly errors.

Would you like to learn more about protecting your assets and minimizing taxes? Schedule a free strategy session here: 👉 https://aba.link/4frh

Chapters:
0:00 Intro
2:00 Do You Have to Claim Social Security When You Retire?
2:39 Social Security Strategies for Married Couples
3:24 Social Security at 62 vs. 67 vs. 70
4:25 How Much Social Security Could You Receive?
5:30 The Social Security Break-Even Point
7:00 Building a Reliable Retirement Income Floor
8:00 How Social Security Benefits Are Taxed
10:36 Retirement Tax Brackets & Roth Conversions
11:32 When Roth Conversions Actually Make Sense
12:34 Qualified Charitable Distributions in Retirement
13:51 The Retirement Income Retirees Forget About
16:09 The Medicare IRMAA Surcharge Surprise
17:55 Medicare at 65: What Retirees Need to Know
19:11 Medicare Parts A, B, C & D Explained
21:00 Medicare Advantage vs. Medigap
22:37 Why Retirees Are Afraid to Spend Their Money
25:59 Is the 4% Retirement Rule Too Conservative?
27:33 The Biggest Fear Retirees Face
31:06 The Truth About Long-Term Care Statistics
32:23 Will Social Security Run Out of Money?
33:03 Final Retirement Takeaways
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FREE TAX & ASSET PROTECTION WORKSHOP
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Trader Status has far more tax-saving potential than most investors realize, going well beyond basic investment deductions in this insightful conversation with tax experts Toby Mathis and Jeff Cottle from Anderson Advisors.

Interested in learning more about tax strategies for traders? Schedule a free consultation here 👉 https://aba.link/mwi8

Learn the key differences between an investor and a trader under IRS rules and why qualifying for Trader Tax Status can allow you to deduct expenses like software, education, and trading equipment. 

They'll breaks down how active traders can potentially save thousands in taxes by being treated as a business instead of a passive investor. 

If you trade stocks, options, or crypto, this is essential tax planning information you need to know.

Show Notes:
0:00 Intro
3:43 The Problem With Investment Expense Deductions
4:48 How the IRS Defines a Trader
6:31 Why Trader Status Often Fails in Tax Court
8:56 What Expenses Traders Can Write Off
10:11 Can Traders Deduct Trading Losses?
11:56 Mark-to-Market Election Explained
13:16 The Hidden Risks of Mark-to-Market Accounting
15:11 Investor vs Trader vs Mark-to-Market Comparison
16:51 The “Unicorn” Strategy Using Business Entities
18:11 How a C Corporation Management Structure Works
20:11 Reducing Taxes With Management Fees
23:11 Guaranteed Payments to a Corporation Explained
26:21 Asset Protection Benefits for Traders
28:11 Estate Planning With LLCs and Trading Accounts
29:31 Final Thoughts
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FREE TAX & ASSET PROTECTION WORKSHOP
Register for an upcoming workshop today if you want to protect your business and personal assets from snoopy lawyers and creditors. Save Your Seat 👉 https://aba.link/7538cb

In this episode, Anderson attorneys Amanda Wynalda, Esq., and Eliot Thomas, Esq., answer listener questions on tax planning, entity structuring, and asset protection for real estate investors. They discuss the best tax strategies for investors who own multiple rental properties as sole proprietors and examine whether converting an S Corporation that owns rental property into an LLC could trigger property tax reassessments or other tax consequences. Amanda and Eliot also explain the rules surrounding home office deductions, including using a detached ADU as a dedicated workspace and claiming deductions for business storage in a garage. They cover the differences between operating as an S Corporation with an accountable plan versus filing on Schedule C, addressing common concerns about IRS scrutiny. Finally, they explore the complexities of structuring a 1031 exchange alongside a self-directed Solo 401(k), highlighting prohibited transaction rules, financing considerations, and strategies for staying compliant while maximizing tax benefits. Tune in for practical guidance on protecting your investments and making informed tax decisions.

Submit your tax question to taxtuesday@andersonadvisors.com

Register for an upcoming workshop today if you want to protect your business and personal assets from snoopy lawyers and creditors. https://aba.link/6rzu

Would you like to learn more about protecting your assets and minimizing taxes? Schedule a free strategy session here: https://aba.link/5c0cf7

Highlights/Topics:

0:00 Intro

9:29 I work in a family-owned company and have the opportunity at the end of this year to obtain equity/ownership. Would you recommend accepting that ownership under a specific tax strategy or corporate setup, or just accepting the ownership under my name and Social Security number?

18:26 Is it a good idea to pull money from a traditional IRA early and then invest in oil funds to get IDC deductions to help offset the taxes I will incur by withdrawing from the IRA?

23:25 Can tax documents be reviewed for previous years and if my previous preparer didn’t use all the available strategies; can those strategies be applied for those years?

27:32 I will be relocating to South Africa which has a tax treaty with the United States Government. I am a retiree who receives a monthly annuity. Will I be double taxed? I will be paying both federal and state taxes in the USA.

34:36 What is the best tax strategy for sole proprietor ownership of 12 rentals?

40:50 I have a 22-unit condo project that we converted into rentals in 1992. It was a C Corp. Now it is an S corp. One adviser suggested converting to an LLC. Would this trigger a taxable event for property tax assessments?

47:23 I have a detached ADU in my backyard. I want to use it as a home office. Can I do that and if so, how is the deduction calculated? Also, can I get a deduction if I use part of my garage for the business for storage?

53:59 Does a Sub-S election with an accountable plan attract more attention than a Schedule C filer?

57:07 We are completing a 1031 exchange and would like guidance on the best way to structure the purchase of our replacement property. Our objective is to use all available 1031 exchange proceeds while funding the remaining balance with assets from a self-directed Solo 401(k), if permissible, and avoid obtaining a conventional mortgage. Are there any IRS rules, prohibited transaction concerns, or tax implications we should be aware of before proceeding?

Want to build a million-dollar retirement without guessing on stocks? In this video, Toby Mathis, Esq. is joined by Eliot Thomas, Esq. of Anderson Business Advisors to break down how the type of account you use—like a taxable brokerage account versus an IRA or 401(k)—can make a massive difference in how fast your money grows. 

Would you like to learn more about protecting your assets and minimizing taxes? Schedule a free consultation here 👉 https://aba.link/zpgs

Register for a FREE upcoming workshop today if you want to protect your personal assets from creditors. Save Your Seat 👉 https://aba.link/puv3 

You’ll learn how taxes impact your investments, and why strategies like tax deferral and Roth accounts can help you keep more of what you earn. 

They also cover how certain plans let you contribute far more than most people realize, sometimes even hundreds of thousands per year. 

If you’re serious about growing your wealth and understanding how retirement accounts actually work, this is a must-watch.

Show Notes:

00:00 Introduction
1:18 Why Most People Never Reach $1 Million for Retirement
3:42 The Truth About Retirement Millionaires
6:15 The Power of Consistent Investing
9:30 Common Mistakes That Destroy Wealth
13:05 Tax Strategies That Accelerate Growth
17:20 Building Multiple Income Streams
21:10 Creating a Long-Term Retirement Plan
24:05 Final Takeaways

In this Tax Tuesday episode, Anderson Advisors' Barley Bowler, CPA, and Eliot Thomas, Esq., answer listener questions covering entity structuring, real estate tax planning, investing, and charitable giving strategies. They explain when it makes sense to form an LLC or S Corporation for a real estate flipping business and whether new investors should wait until after closing their first deal. They also discuss how profits earned inside an LLC trading stocks and stock options are taxed, and whether leaving funds in a brokerage account changes the tax treatment.

Barley and Eliot break down whether a cost segregation study makes sense for a long-held commercial property undergoing significant capital improvements, and how that decision compares to selling the property, completing a 1031 exchange, and performing a cost segregation study on replacement assets. They also explore tax-efficient charitable giving strategies, including ways to contribute appreciated assets or funds designated for charity while minimizing capital gains taxes. Tune in for practical guidance on these tax-saving strategies and more!

Submit your tax question to taxtuesday@andersonadvisors.com

Resources

Claim Your FREE 45-minute Strategy Session to receive business planning tips and asset protection. 👉 https://aba.link/84ac54 

TAX TUESDAY LIVE Toby Mathis, Esq. and his guest will answer ALL your tax questions LIVE on Tax Tuesdays every other Tuesday entirely FREE. 👉 https://aba.link/5a5z 

Register for our Free Tax & Asset Protection Workshop 👉https://aba.link/t5n1

Chapters:

0:00 Intro

9:32 Please speak about vacation rentals that are considered primary residences. We will rent our new property out in the summer months while we are at our secondary residence and stay there in the winter months (so we can’t take advantage of the STR loophole). What tax strategies are available to us in the above case?

17:03 We are selling our company at the end of July 2026. Usually this would be treated as long-term capital gain (taxed at 23.8%) but because I haven't been with the company for 12 months, I believe I would be taxed as ordinary income. Could I invest those funds in a Qualified Opportunity Zone to avoid paying ordinary taxes? Are there new rules with OBBBA that will take effect January 1, 2027?

27:03 I have a C Corporation that earns income from management fees normally paid annually from the LLCs the C Corp manages. During the last C Corp fiscal year, no management fees were paid due to the LLC not having income. Does the C Corp still need to file a tax return if it has no income, and does this mean the C Corp cannot pay any reimbursements for this tax year?

31:45 Please explain the details of when you sell a stock at a loss and repurchase the same stock within 30 days. (Wash Sale Rules)

35:57 At what point do I need to form an LLC or S-Corp for my real estate flipping business? I am just starting in the market and was told not to worry about it until I made my first deal. Is that true?

39:45 I have an LLC for trading stock options and stocks. If I make $1,000,000 profit and do not transfer it out of my brokerage account to me personally, is this money taxed, or is it taxed when I do pull it out of the account?

45:15 I am the managing partner of a general partnership that owns a strip center for many years with little depreciation left. We are spending about $500,000 on a new roof and paving to put a big-box tenant in a long-standing vacancy. Would a cost segregation study benefit here? Should we sell (at a massive profit) and 1031 into new assets and then do the CSS?

51:09 Is there a way to put funds into an account for charity and it not be taxed on gains?

57:23 Can you please explain the non-AFS 417(c) method? Can it be used for an LLC partnership? And can it be used to create a loss, or does the loss carry over to the following tax year?

Interested in learning how to hide your real estate with a land trust? Schedule a free consultation here: https://aba.link/rcvw

In this podcast, Toby Mathis sits down with attorney and asset protection expert Amanda Wynalda to explain why keeping your real estate ownership public can put your finances, privacy, and future at risk.

You’ll learn how lawsuits really happen, why newer investors are often the most vulnerable, and how a single bad tenant situation can spiral into hundreds of thousands of dollars in legal costs.

Toby and Amanda break down how to use land trusts, LLCs, insurance, and privacy strategies work together to help protect real estate investors from unnecessary exposure.

They also explain who actually needs these strategies, common mistakes investors make, and how to create multiple layers of protection around your assets before problems happen.

FREE TAX & ASSET PROTECTION WORKSHOP Register for an upcoming workshop today if you want to protect your business and personal assets from snoopy lawyers and creditors. Save Your Seat: https://aba.link/jyn9

Highlights/Topics:

0:00 Intro
1:51 Who Actually Needs Real Estate Privacy?
3:14 The “Invisible Wall” Asset Protection Strategy
6:13 Real Case Study: Anonymous Investor vs Public Owner
9:12 How Anonymous Ownership Changes Settlements
12:29 Land Trusts vs LLCs Explained
13:00 What Is a Land Trust?
15:24 Attorney Trustees vs LLC Trustees
17:52 Why Land Trusts Need LLCs for Protection
19:59 Biggest Mistakes Investors Make With Land Trusts
22:48 Are Land Trusts Enough By Themselves?
24:45 Can You Use This Strategy In Every State?
26:19 Common Asset Protection Mistakes To Avoid
34:35 How To Get Property Out of Your Personal Name
37:00 Outro

Would you like to learn more about protecting your assets and minimizing taxes? Schedule a free consultation here: https://aba.link/964265

Today, we're discussing a significant tax credit, the Eligible Automatic Contribution Arrangement (EACA), which means actual dollars in your pocket, not just a tax deduction.

Savannah Wallace, one of our expert attorneys, joins to explain how this finance strategy can help you save money on taxes. This is crucial personal finance information for anyone looking to optimize their tax planning.

Don’t miss this opportunity to reduce your tax bill and build wealth smarter.

Sign up for a Free Tax & Asset Protection Workshop here: https://aba.link/lx3q

Join Eliot Thomas, Esq. and Amanda Wynalda, Esq. for this Tax Tuesday replay as they discuss whether you can use a 1031 exchange to buy land for a subdivision, key IRS rules to know, and common mistakes investors should avoid.

Sign up for a Free Tax & Asset Protection Workshop

https://aba.link/775860

Schedule Your FREE Consultation

https://aba.link/j3iq

 

Show Notes:

0:00 Intro

 

8:57 If I sell a rental property, how can I do so, without having to pay capital gains and recapture all the depreciation, or at least minimize the effect of that cash impact? After those tax expenses we will not have much cash left from the sale, if any. Since we only have 1 rental there isn't anything to roll the money into or offset the gains.

 

18:59 Can I use money from a 1031 exchange to buy land from a lot from another property I subdivide?

 

21:22 Should I report my capital gains under my name or set up an LLC?

 

26:10 We are considering purchasing an Airbnb and/or a college rental. We just established an LLC and Trust with Anderson. What are the tax considerations/implications for this?

 

34:17 When is real estate professional status not beneficial?

 

40:42 I have an S corporation and am trying to determine what a reasonable wage for myself would be. How do I determine a reasonable wage?

 

48:11 What is the best tax strategy for your S corporation business renting from yourself? Is it better to lower the rent to yourself and have less rent deduction from 1120S? Are there tax deductions other than property tax and maintenance? Should I form an LLC as a landlord to my business? Or will it make more work filing?

 

56:24 Are there any ways to shelter interest earned from hard-money lending if the money was lent from personal savings, not under any business entity?

 

59:15 What can I file to maximize my tax benefits as a 1099 independent contractor?