Real Estate Strategies Episodes

Democrats won Congress. Your 100% bonus depreciation didn't change. Three depreciation deadlines did not care who won, and one of them lands in 2026. In this solo news episode, David Wiener, Mr. Cash Flow, sorts every post-election tax headline into three buckets (law, proposal, or needs a signature) and walks through what the midterms mean for bonus depreciation, cost segregation, Section 179D, the R&D tax credit and the new qualified production property deduction for factory buildings under Se...

A charitable remainder trust lets you sell an appreciated building with no tax due at closing, reinvest every dollar, and collect income for life. The trade: what is left goes to a charity you pick, not your kids, and the tax does not disappear. It reaches you a slice at a time, in an order the tax code sets. In this solo episode of The Tax Strategy Playbook, David Wiener, Mr. Cash Flow, explains how a charitable remainder trust works in plain English: the charitable remainder annuity trust (CR...

Rental property depreciation is the one deduction the IRS counts against you whether you take it or not. Here's how yours is calculated, line by line. In this solo episode of The Tax Strategy Playbook, David Wiener, Mr. Cash Flow, walks through real estate depreciation from the beginning. You'll see what goes into your cost basis and what stays out, how to split land from building using your county assessor's ratio instead of a flat 20 percent guess, why the clock starts on the placed in servic...

Cost segregation is a real estate tax deduction many of the largest property owners never use. The reason has nothing to do with money. David Wiener, Mr. Cash Flow, sits down with DJ Van Keuren, founder of the Family Office Real Estate Institute and co-founder of Evergreen Property Partners, who has spent 25 years inside family office real estate. They cover why a cost segregation study so often never reaches the people who make the decisions, who actually brings a new tax strategy to a wealthy ...

Mobile home park investing has a cost segregation edge most real estate investors never see. On most manufactured housing communities the operator owns the land and the residents own their homes, so nearly the whole purchase price sits in roads, utility lines, pads, and site work instead of a 27.5 year building. Run an engineering-based cost segregation study on that and 40 to 80 percent of the purchase price can land in 15-year land improvements that qualify for 100% bonus depreciation in year ...

Form 3115 is the four-page IRS form that lets you catch up every dollar of depreciation you should have taken on a rental or commercial building since the day it was placed in service, all on one current return, with no amended returns at all. Bought the property years ago and never had a cost segregation study done? You did not miss your window. In this episode of The Tax Strategy Playbook, David Wiener, Mr. Cash Flow, walks through the cost segregation look back study and the machinery behind...

A self-directed IRA lets you use old retirement money to buy real estate, fund private loans, and invest in businesses, tax deferred or even tax free. Most investors have never been told this account exists. That old 401(k) from a job you left years ago? It could be working a lot harder for you. In this episode of The Tax Strategy Playbook, I sit down with Daniel Tercey, senior account executive at Directed IRA, to walk through the whole roadmap in plain English. You'll learn what "self-directe...

Can a cost segregation study rescue a bad real estate deal? No. But cost segregation can turn a marginal rental property into a genuinely good one for the right investor, and this episode shows exactly where that line sits, with real numbers. It started with a Reddit post: close on the deal, do a cost seg study, and let the depreciation bail you out. Hundreds of upvotes. It's wrong, and believing it can cost you real money. David Wiener, Mr. Cashflow, breaks down what a cost seg study actually ...

A cost segregation audit isn't an accusation. It's a request for proof. Here's the IRS's own checklist (Pub. 5653) so your study passes every time. David Wiener breaks down the IRS Cost Segregation Audit Techniques Guide (Publication 5653) and the 13 elements examiners use to evaluate every study. You'll see exactly what an information document request looks like and why accuracy-related penalties can turn a saved deduction into a five-figure loss. What you'll learn: • Why cost segregation stu...

The conversation explores the critical role of tax strategy in investment decisions, emphasizing the importance of tax mitigation and exit planning. It delves into the distinction between planning for taxes and reacting to taxes, highlighting the impact of tax strategy on long-term wealth. Additionally, it discusses cost segregation, 1031 exchanges, challenges, and the use of Delaware Statutory Trusts (DSTs) as an alternative option. The conversation covers various real estate investment options...

Most investors think they’re buying cash flow, but the ones who really build wealth know the deal either works after taxes, depreciation, and the exit… or it never worked at all. In this episode of The Tax Strategy Playbook, David Wiener (“Mr. Cash Flow”) and Lane Kawaoka (founder of The Wealth Elevator) rip apart the myths that keep real estate investors stuck in mediocre deals and show how high-net-worth investors really structure portfolios using syndications, alternative assets, and smarter ...

Cost segregation myths could be costing you tens of thousands of dollars in taxes you don't actually owe. In this episode of the Tax Strategy Playbook, David Wiener (Mr. Cash Flow) puts 5 of the most common cost segregation myths up against the actual numbers and shows exactly which owners end up paying more simply because they never checked. You'll get the exact cost basis threshold, $150,000, that determines whether an engineering-based cost segregation study is worth running on your property...

I want you to sit with one number: $177,500. That's the tax bill one of my clients avoided entirely, not through a loophole, but by understanding how step-up in basis actually works for real estate investors. In this episode of The Tax Strategy Playbook, I walk through the 5 best assets you can leave your heirs and the 5 worst estate planning traps real estate investors fall into. These are traps that can cost families six figures in avoidable taxes and legal fees. You'll learn: ✅ How step-up...

Unlock the Power of Opportunity Zones 2.0: A Tax Strategy Nobody's Talking About On July 4, 2025, the landscape of tax incentives for investors and business owners shifted dramatically with the passage of the One Big Beautiful Bill Act, which made Opportunity Zones a permanent fixture in the U.S. tax code. Just over a year later, on June 18, 2026, the IRS released Notice 2026-40, offering crucial transitional guidance for the evolution from Opportunity Zone 1.0 to the newly established Opportun...

Depreciation recapture is the bill that shows up when you sell a property you've depreciated, and a cost segregation study makes a bigger slice of it come back at ordinary income rates. That's not a reason to skip the study. It's a reason to plan the exit before you take the deduction. In this solo episode of The Tax Strategy Playbook, David Wiener, Mr. Cash Flow, walks through the back half of cost segregation that almost nobody talks about: what happens when you sell. What's covered: Why ev...

Tax Traps. Most real estate investors often get crushed not by bad deals, but by poor tax decisions they weren't even aware of. This video features a former IRS senior trial attorney who shares insights on how common tax pitfalls, such as incorrect entity choices or inadequate documentation, can lead to significant financial losses during a tax audit. Understanding proper tax planning and tax strategies is crucial for business owners to avoid IRS red flags and protect their wealth. In this episode of The Tax Strategy Playbook, host David Wiener (Mr. Cash Flow) sits down with Scott Estill, a former IRS Senior Trial Attorney turned nationally recognized tax attorney, speaker, and author, to expose 7 real estate tax traps quietly destroying real estate investor wealth in 2026.

Tired Landlords: Escape $1M Tax Bills with a DST 1031 Exchange Are you a real estate investor feeling the exhaustion of active property management? Do the recurring challenges of tenants, toilets, and trash weigh on you, while the thought of selling your appreciated assets fills you with dread over massive capital gains and depreciation recapture taxes? If you're sitting on hundreds of thousands, or even millions, in potential tax liabilities, know that you're not alone, and there is a strate...

Tax Strategy vs TikTok Hacks: 7 Viral Myths That Trigger Audits Are you tired of scrolling through TikTok and seeing “tax hacks” and viral write-off tricks that could actually land you in hot water with the IRS? In this episode of The Tax Strategy Playbook, host David Wiener, also known as “Mr. Cash Flow,” cuts through the noise. He exposes 7 common social media tax myths that are actually audit bait and reveals the legitimate, long-term tax strategies that wealthy investors use instead. If yo...

The short term rental tax loophole is how a high-income W-2 earner or business owner can use rental losses against wages and business income without qualifying as a real estate professional. Pair it with a cost segregation study and 100% bonus depreciation, and one property can produce a first-year loss big enough to matter on a six-figure return. In this episode of The Tax Strategy Playbook, David Wiener, Mr. Cash Flow, sits down with Ryan Bakke, CPA, real estate investor, and founder of Tax S...

What if you could sell a rental property, defer 100% of your capital gains tax and depreciation recapture, and roll every dollar into a bigger, better deal, then keep doing it forever? That's exactly what a 1031 like-kind exchange allows real estate investors to do. In this episode of The Tax Strategy Playbook, host David Wiener sits down with Dave Foster, founder of The 1031 Investor and one of the country's leading experts on 1031 exchange strategies. Dave breaks down the exact rules, timelin...

This episode dives into how landlords use real estate to build durable wealth and tax efficiency, featuring investor, broker, and educator Christian Walsh. Christian shares his journey from traditional real estate work into becoming a trusted guide for everyday investors who want to play the game more strategically. He breaks down how to think like a long-term investor, why understanding local market dynamics matters more than chasing national headlines, and how to structure deals so they actually support your lifestyle and goals. You’ll hear practical examples of using leverage wisely, positioning yourself for opportunities in shifting markets, and avoiding the common mistakes that keep investors stuck. The conversation also touches on building a personal brand as an agent or advisor, communicating clearly with clients, and creating content that attracts serious investors instead of tire-kickers. By the end, listeners walk away with a clearer blueprint for growing a resili…

The 2025 Tax Bill, officially known as the One Big Beautiful Bill, is the biggest tax law change in nearly a decade. And most small business owners and real estate investors are about to sleepwalk right past it. In this episode of The Tax Strategy Playbook, host David Wiener breaks down exactly what the One Big Beautiful Bill means for small businesses, real estate investors, rental property owners, and entrepreneurs, and how to turn these new tax law changes into a concrete action plan before ...

Most real estate investors assume a cost segregation study automatically creates a tax win. But if the IRS classifies your rental activity as passive, those losses may be trapped, unable to offset your W-2 income or active business income the way you expected. In this episode of The Tax Strategy Playbook, David Wiener and CPA Gabriel Virdaru break down the passive vs. active deduction rules in plain English. You'll learn exactly how the IRS distinguishes passive income from active income, why...

Choosing the wrong entity structure is one of the most expensive mistakes real estate investors and small business owners make, and most don't find out until it's too late. In this episode of The Tax Strategy Playbook, host David Wiener sits down with Matt Bontrager, CPA and managing partner of TrueBooks, a firm that works almost exclusively with real estate investors and entrepreneurs. Matt has reviewed hundreds of real-world LLC and S corp structures and pulls back the curtain on how entity s...