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Real Estate Investors, Stock Traders, and Business Owners guide to preserve their wealth, protect their assets, and prosper in the future.
Episodes
Tuesday Mar 10, 2026
Tuesday Mar 10, 2026
In this episode, Anderson attorneys Amanda Wynalda, Esq., and Eliot Thomas, Esq., answer listener questions on a wide range of real estate and tax topics. They cover tax benefits available for raw land purchases, including property tax deductions under SALT and investment interest expense on Schedule A. They explain the IRS tax code reference for short-term rentals — IRC Section 469 and Treasury Regulation 1.469-1T — and address special considerations for Airbnb-type rentals in foreign countries, including the mandatory alternative depreciation system (MADS) and foreign tax credits. Amanda and Eliot discuss minimum purchase prices for cost segregation studies and highlight property types like RV parks, car washes, and convenience stores that offer strong bonus depreciation benefits. They tackle the vacation home standard deduction question, clarifying how Schedule E rental properties interact with itemized deductions. The episode dives deep into multiple 1031 exchange questions, including timelines for entering a second 1031, California's clawback provisions on out-of-state replacement properties, and the drop-and-swap strategy for LLC partnerships. They also explain how to navigate delayed IRS refunds using the Taxpayer Advocate Service, and break down the time limits and rules for changing LLC tax status, including Form 8832 and the five-year rule. Tune in for expert advice on these topics and more!
Submit your tax question to taxtuesday@andersonadvisors.com
Highlights/Topics:
- 00:00 — Intro
- 07:06 — "We recently made a large land purchase. Are there any tax benefits we can claim against our income?" — Deduct property taxes under SALT and investment interest expense on Schedule A.
- 14:27 — "Is there an IRS tax code reference I can look at for short-term rentals?" — Yes: IRC Section 469 and Treasury Regulation 1.469-1T define short-term rental rules.
- 18:20 — "Any special considerations for short-term Airbnb-type rentals in foreign countries?" — Use mandatory ADS depreciation; claim foreign tax credits to avoid double taxation.
- 22:55 — "Is there a minimum purchase price you recommend for STRs? Also, what type of property is ideal?" — A building value of $150,000–$300,000 is an ideal cost segregation starting point.
- 28:21 — "With today's Individual Standard Income Tax Deduction now so high, how can a Schedule E Vacation Home still be a tax advantage when write-offs no longer exceed the Standard Deduction?" — Schedule E rental deductions are entirely separate from your standard deduction benefit.
- 35:46 — "I sold one investment property and bought two under a §1031 exchange. When can I sell the two §1031 exchange replacement properties and enter a new §1031 exchange without a tax penalty?" — Hold replacement properties at least two years and thoroughly document your rental intent.
- 41:15 — "If a property is sold in California in a §1031 exchange and the replacement property in Tennessee is later sold through a second §1031, does California have capital gains taxes that need to be paid?" — Yes; California tracks deferred gains annually on Form 3840 until the tax is due.
- 44:34 — "If you have an LLC partnership with 3 members that recognized a sale, can each member make their own election with respect to a 1031 exchange? Or must the entire entity participate in the replacement property?" — Use the drop-and-swap strategy carefully; the IRS watches closely for step transactions.
- 49:15 — "In June of last year, the IRS asked me to submit my previous taxes before receiving my current tax refund. I did so. When I check the IRS website periodically, it says my refund is delayed. I have attempted to call, but no answer from the IRS. How do I expedite receiving my tax refund? Thank you in advance." — Contact the Taxpayer Advocate Service and review your IRS tax transcripts online.
- 53:18 — "What's the time limit on changing LLC tax status?" — File Form 8832 with an election date up to 75 days back or 12 months forward.
Resources:
Tax and Asset Protection Events
https://andersonadvisors.com/real-estate-asset-protection-workshop-training/?utm_source=how-to-sell-1031-replacement-properties-without-tax-penalties&utm_medium=podcast
Schedule Your FREE Consultation
https://andersonadvisors.com/strategy-session/?utm_source=how-to-sell-1031-replacement-properties-without-tax-penalties&utm_medium=podcast
https://andersonadvisors.com/
https://www.youtube.com/@TobyMathis
https://www.tiktok.com/@tobymathisesq
https://www.youtube.com/@ClintCoons
Thursday Mar 05, 2026
Thursday Mar 05, 2026
In this episode, real estate data expert and multifamily investor Neal Bawa returns for the annual 2026 housing market forecast. Neal breaks down the performance of single-family and multifamily asset classes over the past several years, explaining why rents were essentially flat in 2025 and how the ICE workforce crackdown pushed a wave of unfinished inventory into 2026. He outlines why multifamily prices have hit a bottom — down 20–30% from their 2022 peak — and why that represents a buying opportunity, while single-family prices have remained surprisingly resilient due to the mortgage lock-in effect.
Neal also shares his prediction of a rental supply shortage in 2027–2028 that should drive rent growth and occupancy higher, offers frank advice to syndication investors on holding through the downturn, and explains why small interest rate cuts can have an outsized impact on equity. He also introduces AI as a major wildcard that could reshape housing demand beyond 2030. Tune in for data-driven insights and practical takeaways for investors at every level.
Highlights/Topics:
- 0:00 Intro + welcome Neal Bawa (2026 real estate predictions)
- 0:34 Single-family vs multifamily explained (Class A/B/C framework)
- 1:32 Real-world rent drop example: Fresno & Madera inventory surge
- 2:30 2025 rent growth recap: flat year, concessions, inflation effect
- 4:36 2026 forecast: supply rolling over, Q1 weak then accelerating rent growth
- 6:26 Investor question: should you buy now or sit on the sidelines?
- 7:11 Multifamily vs single-family since 2022: prices, resilience, lock-in effect
- 10:11 Why single-family cash flow is hardest right now (rates, taxes, insurance)
- 11:08 Why multifamily is near the bottom + “great time to buy” thesis
- 13:39 2027–2028 outlook: coming rental supply shortage + rent/occupancy boost
- 19:50 The AI wildcard: demand, jobs, and what changes after 2030
- 22:00 Advice for syndication investors: hold, cash calls, protect equity
- 24:16 Interest rates + equity math: why small rate cuts matter a lot
- 27:24 The “emotion” factor: sentiment shift and opportunity in 2026
- 32:00 Wrap-up + Neal’s free webinars at multifamilyu.com/club
- Share this with real estate investors you know
Resources:
Multifamily University Investor Club — Free webinars (8/year), no upsell, no subscription https://multifamilyu.com/lp/multifamily-university-investor-club-lp/
Grocapitus — Neal Bawa's investment company https://www.grocapitus.com
Location Magic eBook — Neal Bawa's data-driven market selection resource https://multifamilyu.com/lp/location-magic-ebook/
https://andersonadvisors.com/
https://www.youtube.com/@TobyMathis
https://www.tiktok.com/@tobymathisesq
https://www.youtube.com/@ClintCoons
Tuesday Feb 24, 2026
Tuesday Feb 24, 2026
In this Tax Tuesday episode, Anderson's Barley Bowler, CPA, and Eliot Thomas, Esq., address listener questions on a wide range of tax strategies for real estate investors, business owners, and healthcare professionals. They explain how seller financing affects the ability to use cost segregation and bonus depreciation under IRC Section 465's at-risk rules, and how a single-member LLC can recoup startup education costs through a C Corporation structure with shareholder loans. Barley and Eliot walk through the powerful tax advantages of setting up a management C Corporation over a Wyoming holding company — including medical reimbursements, accountable plan deductions, and W-2 solo 401(k) options. They cover what Medicare premiums and COBRA costs are reimbursable through a C Corp's medical reimbursement plan, how the Section 121 exclusion works for primary residence sales, and what options exist for mitigating a seven-figure business sale gain. Other topics include write-offs for uncollected insurance balances in healthcare practices, avoiding required minimum distributions by rolling into an employer plan, and electing pass-through entity tax in New York for investment partnerships. Tune in for expert guidance on these strategies and more!
Submit your tax question to taxtuesday@andersonadvisors.com
Highlights/Topics:
7:18 — "How does the use of seller financing impact the ability to use strategies such as cost segregation and bonus depreciation?" Under IRC Section 465, your deductible losses are limited to the amount you have personally at risk. First phrase: "This is a great question. This covers a lot of different angles."
15:27 — "The business failed to make any profit in year 1. How are those initial costs recouped, and how much can be carried forward to future years?" A C Corp election allows full education deductions; fund via shareholder loan for tax-free recoupment. First phrase: "A single member LLC spent $9,500 on training and other related startup costs."
21:06 — "If I operate one LLC per real estate project, does it make sense to have a separate management entity to deduct shared expenses like an assistant, office costs, business meals, travel, and pre-development work? What's the correct tax structure?" A management C Corporation reduces rental income and allows tax-free reimbursements to the owner. First phrase: "If I operate one LLC per real estate project, does it make sense to have a separate management entity..."
27:45 — "What components of Medicare premiums are reimbursable by my property management C corporation?" Out-of-pocket Medicare and COBRA premiums qualify; general wellness supplements typically do not. First phrase: "What components of Medicare premiums are reimbursable by my property management C Corporation..."
38:10 — "If I sell my house, how long do I have to buy something else before I owe capital gains tax? Do I need to purchase the next home for more than the sale of the house or is there a percentage of that value?" Section 121 excludes up to $250K single or $500K married with no replacement property required. First phrase: "If I sell my house, how long do I have to buy something else before I owe capital gains tax?"
44:45 — "For my healthcare practice, where can I write off balances that insurance refuses to pay, and promotions/certain population deals where I give service discounts or free visits/supplement packages for charity events?" Cash-basis taxpayers cannot deduct uncollected income, and donated services are not tax-deductible. First phrase: "For healthcare practice, where can I write up balances? Insurance refuses to pay."
50:02 — "Can I avoid taking Required Minimum Distributions at age 73, if I roll over my retirement contributions from a previous employer's plan to my current employer's plan?" Rolling into a current employer plan may defer RMDs if you are not a greater-than-5% owner. First phrase: "Can I avoid taking required minimum distributions at age 73?"
53:12 — "Can an investment partnership elect the Pass Through Entity Tax in New York? What are the issues creating/dissolving investment partnerships?" New York allows any partnership to elect PTET, generating a valuable federal-level tax deduction. First phrase: "Can an investment partnership elect the pass through entity tax in New York?"
59:38 — "I sold my company, and I am coming into a 7-figure settlement soon. What can I do with that money to decrease my taxes?" Explore charitable remainder trusts, qualified opportunity zones, and capital loss harvesting strategies. First phrase: "I sold my company and I'm going to come into a seven figure settlement soon."
Resources:
Tax and Asset Protection Events — Live workshop in Las Vegas, March 19–21
https://andersonadvisors.com/real-estate-asset-protection-workshop-training/?utm_source=how-to-structure-a-tax-efficient-management-entity&utm_medium=podcast
Schedule Your FREE Consultation — Scan the QR code or visit the link to book your strategy session
https://andersonadvisors.com/strategy-session/?utm_source=how-to-structure-a-tax-efficient-management-entity&utm_medium=podcast
https://andersonadvisors.com/
https://www.youtube.com/@TobyMathis
https://www.tiktok.com/@tobymathisesq
https://www.youtube.com/@ClintCoons
Tuesday Feb 17, 2026
Tuesday Feb 17, 2026
In this episode, host Toby Mathis, Esq., speaks with returning guest Chris Streit, a cost segregation expert from CSA Partners, about two frequently overlooked tax strategies that can save real estate investors thousands of dollars: Partial Asset Dispositions (PAD) and Qualified Improvement Property (QIP). They discuss how PAD allows investors to immediately expense the remaining value of replaced building components like roofs, rather than continuing to depreciate both the old and new assets simultaneously. Chris explains how QIP enables investors to leverage 100% bonus depreciation on commercial property improvements made after January 19, 2025, including improvements to short-term rentals.
The conversation covers the critical timing of converting long-term rentals to short-term rentals before making improvements, the necessity of cost segregation studies for substantiating these deductions, and real-world applications for various commercial properties including hotels, restaurants, and retail spaces. Toby and Chris also address common concerns about IRS audits and emphasize the importance of working with specialized professionals to maximize these often-missed deductions.
Highlights/Topics:
- (00:00) Understanding partial asset dispositions and roof replacements
- (07:11) Qualified improvement property explained for commercial assets
- (11:18) Converting long-term rentals to short-term
- (18:31) Bonus depreciation timeline and audit concerns
- Share this with business owners you know
Resources:
📊 Cost Segregation Resources: Request a FREE Cost Segregation Benefit Analysis: https://aba.link/83c5ab Learn more about CSA Partners: https://csap.com/
🎥 Related Videos With Chris Streit:
5 Cost Segregation Mistakes That Trigger IRS Audits: https://youtu.be/1urK1954GS8
Stop Overpaying Depreciation Recapture: The §1245 Move They Skip: https://youtu.be/DBbT2jVG3Js
📚 Download Your Free Resources: Download Your Digital Copy Of Infinity Investing: How The Rich Get Richer And How You Can Do The Same: https://inf.link/efz
Register for an upcoming workshop today to protect your assets from creditors.
Save Your Seat: https://aba.link/6ea4bf
https://andersonadvisors.com/
https://www.youtube.com/@TobyMathis
https://www.tiktok.com/@tobymathisesq
https://www.youtube.com/@ClintCoons
Tuesday Feb 10, 2026
Tuesday Feb 10, 2026
In this episode, Anderson attorneys Amanda Wynalda, Esq., and Eliot Thomas, Esq., tackle listener questions on tax strategies for real estate investors and traders. They explain the tax implications of house flipping, including when to report income and how installment sales affect taxation. Amanda and Eliot discuss transitioning from a disregarded LLC to an S Corporation for managing rentals and flipping properties, emphasizing the importance of avoiding dealer status. They dive deep into 1031 exchange requirements, including timing constraints, qualified intermediaries, and the rules for converting investment property to a primary residence. Other topics include home office deductions versus reimbursements, deducting mileage for consultants with administrative offices, optimal business structures for active stock trading, differences between S and C Corporations, and the tax consequences of using corporate equipment for personal use. Tune in for expert guidance on maximizing tax savings while maintaining compliance!
Submit your tax question to taxtuesday@andersonadvisors.com
Highlights/Topics:
- [00:00] Intro
- [06:26] I purchased a home for $12,000 in 2025 for flipping. Do I show it on my taxes at all or only after I flip? How do I calculate the taxes from flipping? If I want to sell a flip on installments – how does that change the tax? Report only after sale; calculate as ordinary income plus self-employment tax.
- [10:02[ What do you recommend to transition from a disregarded LLC to S Corp for managing rentals and doing house flipping as well? Use separate S or C Corporation to avoid dealer status.
- [14:10] I'd like to do a 1031 Exchange and eventually move into the property as my primary residence. How quickly can I do that? Wait 24 months with proper rental use before converting to residence.
- [19:03] What are some of the pitfalls of a 1031 exchange to focus on? Timing deadlines, qualified intermediary requirement, and boot recognition are critical pitfalls.
- [29:28] Can my S Corporation pay rent to me for my home office? And if so, is this considered personal income? Use accountable plan reimbursements instead to avoid taxable rental income.
- [33:32] If I am a consultant and take a gig at a company 35 miles from my S-Corporation's administrative office, can I write off the costs to get to the facility on the days I work there? Yes, with administrative office, mileage becomes deductible business travel expense.
- [36:41] What's the best business structure setup for active stock trading? Limited partnership with C Corporation general partner provides optimal tax benefits.
- [42:19] What are the differences between an S Corporation and a C Corporation for an LLC? S Corporation flows through; C Corporation pays flat 21 percent rate.
- [47:25] If I move equipment into my C corporation, can I still use it for personal use? Personal use over 50 percent creates taxable fringe benefit complications.
Resources:
Tax and Asset Protection Events
https://andersonadvisors.com/real-estate-asset-protection-workshop-training/?utm_source=1031-exchange-pitfalls-real-estate-investors-must-know&utm_medium=podcast
Schedule Your FREE Consultation
https://andersonadvisors.com/strategy-session/?utm_source=1031-exchange-pitfalls-real-estate-investors-must-know&utm_medium=podcast
https://andersonadvisors.com/
https://www.youtube.com/@TobyMathis
https://www.tiktok.com/@tobymathisesq
https://www.youtube.com/@ClintCoons
Thursday Feb 05, 2026
Thursday Feb 05, 2026
In this episode, Anderson attorney Clint Coons, Esq., sits down with real estate investor Gabriel Hamel to explore creative financing strategies for building wealth without traditional bank loans. Gabriel shares his inspiring journey from working minimum wage after military service to acquiring nearly 400 properties using seller financing and no-money-down techniques. They discuss how to structure creative deals, overcome the misconceptions about creative financing, the importance of cash flow over appreciation, and strategies for analyzing deals that work in any market. Gabriel also explains the power of building relationships, finding motivated sellers, and creating win-win scenarios that benefit both buyers and sellers. Clint and Gabriel emphasize the importance of taking action, getting involved in investment communities, and pursuing time freedom through real estate investing. Tune in to learn how you can start building your real estate portfolio even if you have little to no cash!
Gabriel Hamel joined the military at 17 and deployed to Iraq in 2003-2004. After returning home, he found himself working 30 hours a week at minimum wage with dreams of financial freedom. When the 2008 financial crisis eliminated traditional lending options, Gabriel discovered creative financing and seller financing strategies. Starting in 2009 with his first no-money-down deal, he systematically replaced his minimum-wage income and eventually built a $60M portfolio of nearly 400 properties. Today, Gabriel co-hosts the Zero to 100 Real Estate Podcast, helping investors build wealth designed around freedom, family, and choice.
Highlights/Topics:
- (00:00) - Introduction to Creative Financing with Gabriel Hamel
- (02:08) - First Properties and the 2005-2007 House Hacking Strategy
- (06:08) - The 2008 Financial Crisis: When Banks Said No
- (07:38) - Debunking Creative Financing Myths and Misconceptions
- (10:08) - Finding Motivated Sellers and Structuring Win-Win Deals
- (20:15) - Cash Flow vs. Appreciation: Building Sustainable Wealth
- (30:45) - Analyzing Deals and Making Offers That Work
- (42:49) - The Zero to 100 Tribe: Community and Time Freedom
- (45:46) - Taking Action: Final Advice for Aspiring Investors
Resources:
Connect with Gabriel 👇
http://www.zeroto100tribe.com/
https://www.instagram.com/the_real_gabriel_hamel
https://podcasts.apple.com/us/podcast/the-zero-to-100-real-estate-podcast/id1745322778
Schedule Your FREE Consultation
https://aba.link/0qx
Tax and Asset Protection Events
https://aba.link/2f2856
https://andersonadvisors.com/
https://andersonadvisors.com/podcast/
https://www.youtube.com/channel/UC5GX-U6VbvMkhSM1ONBiW8w
Anderson Advisors Tax Planning Appointment
https://andersonadvisors.com/ss/
Thursday Jan 29, 2026
Thursday Jan 29, 2026
In this episode, Toby Mathis, Esq., sits down with 3,700+ unit operator Aaron Adams to discuss the six hottest real estate markets for 2026 and six markets to avoid. They cover the economic factors driving real estate growth, including GDP expansion, potential interest rate decreases, and tax bill impacts. Aaron shares his top picks: Kansas City (benefiting from Oracle's massive $28 billion Cerner acquisition), Idaho Falls (emerging nuclear technology hub), Charlotte (continued banking sector growth), the Winston-Salem triad area (affordability with five universities), and Indianapolis (steady lockstep growth in rents, wages, and prices).
On the flip side, they discuss why to avoid Chicago (high property taxes, population decline), San Francisco (rent controls, tenant protections), Detroit (60% population loss, aging infrastructure), New York City (landlord-unfriendly policies), Los Angeles (high acquisition costs, poor cash flow), and Austin (overbuilt multifamily, high insurance and taxes). They also cover the strategy of investing in smaller cities within 30-40 miles of hot metros to capitalize on growth while maintaining affordability. Tune in for expert insights on where to invest for cash flow in 2026!
Highlights/Topics:
- 00:00 - Introduction: 2026 Real Estate Market Outlook
- 01:42 - Economic Convergence: GDP, Interest Rates & Tax Impacts
- 12:30 - Hot Market #1: Kansas City (Oracle's $28B Acquisition)
- 17:02 - Hot Market #2: Idaho Falls & Markets to Avoid: San Francisco
- 23:08 - The 30-Mile Strategy: St. Joseph, MO Example
- 28:16 - Hot Markets #3-5: Charlotte, Winston-Salem & Indianapolis
- 35:31 - Asset Allocation Strategy: The 30-30-30-10 Model
- 40:39 - Markets to Avoid: LA, Austin, Chicago & Detroit
- Share this with business owners you know
Resources:
📚 Download Your Free Resources:
Download Your Digital Copy Of Infinity Investing: How The Rich Get Richer And How You Can Do The Same
https://inf.link/efz
Register for an upcoming workshop today to protect your assets from creditors. Save Your Seat:
https://aba.link/6ea4bf
🏘️ Connect With Aaron Adams:
REI Kickstart Summit Event
https://course.infinityinvesting.com/infinity-summit-interest-update
Alpine Capital Solutions
https://alpinecapitalsolutions.com/
Contact Aaron Adams
https://alpinecapitalsolutions.com/contact/
https://andersonadvisors.com/
https://www.youtube.com/@TobyMathis
https://www.tiktok.com/@tobymathisesq
https://www.youtube.com/@ClintCoons
Tuesday Jan 27, 2026
Tuesday Jan 27, 2026
In this Tax Tuesday episode, Eliot Thomas, Esq., and CPA Barley Bowler address listener questions on diverse tax topics including property management S corporations and QBI deductions. They explain how to structure management companies for rental properties, the relationship between W-2 wages and K-1 distributions, and the power of the 199A qualified business income deduction. Eliot and Barley dive deep into 100% bonus depreciation, cost segregation studies, and depreciation recapture rules—clarifying when to use Section 179 expensing versus bonus depreciation. They also cover maximizing education expense deductions through C corporations, leveraging oil and gas working interest investments for immediate ordinary deductions of 60-85%, structuring private operating foundations with proper payroll procedures, and optimal tax strategies for business sales including the powerful Section 1202 exclusion. Tune in for expert guidance on these advanced tax planning strategies!
Submit your tax question to taxtuesday@andersonadvisors.com
Highlights/Topics:
- 00:00 - Intro
- 05:34 - "I have a property management S corporation for my rental properties. All rents and expenses are paid to/from the S-corporation. I take a W2 from the corporation. At the end of the year I receive a K1 for the net rental income. Can I take a QBI deduction for this K1?" - The K-1 reflects only the management fee, not rental income. QBI applies to that fee.
- 14:07 - "I am curious how I can get the maximum benefit from a tax perspective for education class fees paid." - C corporations can deduct new business education via loans from shareholders arrangement.
- 19:04 - "Please explain 100% Bonus Depreciation recapture and eligible assets with a less than 20 year life being fully depreciated in Year 1." - Cost segregation identifies 5, 7, 15-year assets eligible for immediate bonus depreciation.
- 24:08 - "What happens if you sell a rental property with depreciation recapture after a cost segregation with bonus depreciation?" - Five-year and fifteen-year property recaptures at ordinary rates; building capped at 25%.
- 29:46 - "Please explain Section 179 expensing." - Section 179 allows immediate equipment expensing but cannot create a loss situation.
- 36:20 - "Is oil and gas a good tax deduction?" - Working interest investments provide immediate 60-85% ordinary deductions through intangible drilling costs.
- 40:36 - "My family has a private operating foundation. One family member works full-time for the foundation and we agreed to pay a wage to that individual. Would that family member have a w-2? Or does the owner withdraw? Also payroll?" - Pay reasonable W-2 wages through payroll; no owner withdrawals in nonprofit foundations.
- 44:40 - "What is the best tax strategy for selling a business?" - Stock sales create capital gains; consider Section 1202 for qualified small businesses.
Resources:
Tax and Asset Protection Events
https://andersonadvisors.com/real-estate-asset-protection-workshop-training/?utm_source=100-bonus-depreciation-recapture-explained&utm_medium=podcast
Schedule Your FREE Consultation
https://andersonadvisors.com/strategy-session/?utm_source=100-bonus-depreciation-recapture-explained&utm_medium=podcast%C2%A0
https://andersonadvisors.com/
https://www.youtube.com/@TobyMathis
https://www.tiktok.com/@tobymathisesq
https://www.youtube.com/@ClintCoons
Friday Jan 16, 2026
Friday Jan 16, 2026
In this episode, Toby Mathis, Esq., interviews Chris Streit from CSA Partners about the five critical elements that cause cost segregation studies to fail under IRS audit. Chris, whose firm has completed tens of thousands of cost seg reports, reveals that 80% of studies contain fatal flaws that will not survive scrutiny. The conversation covers the importance of establishing proper real estate professional status or short-term rental qualification before taking accelerated depreciation.
Chris explains why land value allocation is the first thing the IRS examines and how it must use county valuation at time of purchase—not rule-of-thumb percentages. They discuss the non-negotiable requirement for physical site visits with video documentation, the necessity of using current RSMeans software with local jurisdiction pricing (not outdated books or averages), and why having accessible audit support is crucial when the IRS comes calling. Chris emphasizes that the burden of proof is on the taxpayer, making professional documentation and expert backup essential. Tune in to learn how to protect your cost segregation deductions and avoid costly audit failures!
Highlights/Topics:
- (00:00) - Introduction: Why Your Cost Seg Will Fail
- (00:54) - Element #1: Real Estate Professional Status
- (02:46) - Element #2: Land Value Allocation
- (09:06) - Element #3: Engineered Study & Site Visits
- (12:38) - Element #4: RSMeans Cost Data Requirements
- (15:39) - Element #5: Audit Support & Accessibility
- Share this with business owners you know
Resources:
Request a FREE Cost Segregation Benefit Analysis
https://aba.link/vsh
Tax and Asset Protection Events
https://andersonadvisors.com/real-estate-asset-protection-workshop-training/?utm_source=your-cost-segregation-will-fail-audit-if-you-miss-these-5-elements&utm_medium=podcast
Learn more about CSA Partners: https://csap.com/
https://csap.com/
https://andersonadvisors.com/
https://www.youtube.com/@TobyMathis
https://www.tiktok.com/@tobymathisesq
https://www.youtube.com/@ClintCoons
Tuesday Jan 13, 2026
Tuesday Jan 13, 2026
In this episode, Anderson attorneys Amanda Wynalda, Esq., and Eliot Thomas, Esq., tackle listener questions on reducing capital gains taxes and advanced tax strategies for real estate investors and business owners. They explore the intricacies of cost segregation studies and bonus depreciation versus Section 179, including timing issues for renovations. Amanda and Eliot discuss strategies for minimizing capital gains after decades of depreciation, converting ordinary income to capital gains in development deals, and the tax implications of oil and gas working interest investments. The duo also covers deductible expenses for corporate retreats, entity structuring for piano tuning and bookkeeping businesses, and sophisticated trading partnerships using C corporations. Finally, they take a deep dive into Solo 401(k) contribution limits, explaining the differences between employee contributions, employer matches, and the mega backdoor Roth strategy for maximizing retirement savings. Tune in for expert advice on these and more!
Submit your tax question to taxtuesday@andersonadvisors.com
Highlights/Topics:
- "I purchased a rental and did a cost seg in 2024. I renovated it in 2025. Can I use a cost segregation and/or Section 179 to depreciate the new renovation assets in 2025?" Answer: Yes, bonus depreciation works; 179 has limitations.
- [21:16] “How can I reduce capital gains on the sale of a rental property after nearly 27 and a half years? The accelerated depreciation reduced the basis to zero." Answer: 1031 exchange, installment sale, or opportunity zones.
- "How can I get capital gains on my K-1 instead of ordinary income on my investment into a real estate developer corporation?" Answer: Development corporations typically generate ordinary income, not capital.
- "What expenses for an off-site retreat for an LLC member and officers meeting are deductible? For example, travel, lodging, meals, activities." Answer: Travel, lodging, 50% meals if genuinely business-related.
- "If I invest in an oil and gas working interest and I have a first year larger intangible drilling cost loss than is needed for a given tax year based on adjusted gross income, can the excess be carried forward to a future tax year as a net operating loss? Would the NOL have alternative minimum tax implications as well?" Answer: Yes, NOL carries forward; minimal AMT concerns today.
- "How do I set up a holding company in California? I want the holding company to own my two companies. One's a piano tuning business and then a bookkeeping business. I have an average income of $125,000 per year combined: $45K for piano, $80K for bookkeeping." Answer: Wyoming LLC holding company owns two California entities.
- "I want more information on how I can structure my LLC more efficiently for day trading. What can I do to minimize my taxes for the new year? How can I lower my capital gains tax from day trading?" Answer: Trading partnership with C corporation for deductions.
- "Please take a deep dive into Solo 401(k) contributions. What are the individual contribution limits, employer match limits, and especially the voluntary after tax contribution limits. Which components need to be earned income and how does this change if contributing to a Roth 401(k)?" Answer: $72K total; $24.5K employee; mega backdoor uses after-tax.
Resources:
Tax and Asset Protection Events
https://andersonadvisors.com/real-estate-asset-protection-workshop-training/?utm_source=how-to-reduce-capital-gains-taxes-when-selling-a-rental-property&utm_medium=podcast
Schedule Your FREE Consultation
https://andersonadvisors.com/strategy-session/?utm_source=how-to-reduce-capital-gains-taxes-when-selling-a-rental-property&utm_medium=podcast
https://andersonadvisors.com/
https://www.youtube.com/@TobyMathis
https://www.tiktok.com/@tobymathisesq
https://www.youtube.com/@ClintCoons