Cost Segregation Myths vs Reality | Which Owner Pays More?
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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 — and why it applies to residential long-term rentals, short-term rentals, commercial, and industrial properties alike, not just large commercial buildings. David also breaks down why a properly documented, engineering-based study isn't the audit risk people assume: the real risk is the cheap, calculator-based shortcut version, not the strategy itself. CSSI, the cost segregation partner behind this show, has completed more than 65,000 engineering-based studies nationwide without ever triggering an audit.
You'll learn why your tax professional isn't already running this analysis automatically as part of a normal tax return (it takes a separate engineering-based study to unlock it), and why a look-back study means you haven't missed your window even if you've owned the property for years — it can capture missed depreciation going back as far as 15 years without amending a single prior return.
You'll also hear why short-term rentals often qualify even more cleanly than long-term rentals thanks to faster-depreciating furniture, appliances, and finishes, how a 1031 exchange or long-term hold can address depreciation recapture before it becomes a problem, and the exact question David recommends bringing to your tax professional this week — worded so it actually gets you a real answer instead of a shrug.
⏱️ CHAPTERS
00:00 Introduction
01:49 The Promise
03:15 Who This Episode is For
04:16 Why This, Why Now
05:48 Myth #1 - The Big Building Myth
14:31 Myth #2 - The Audit Magnet Myth
19:10 Myth #3 - The Tax Pro Myth
21:08 Myth #4 - The "Too Late" Myth
23:41 Myth #5 - The "Long-Term Rental" Myth
26:44 FAQ
28:43 The Playbook
31:57 Conclusion
If a myth in this episode has been quietly costing you money, share it with one investor or business owner who needs to hear it.
Subscribe to the newsletter for free resources, including the current 2026 tax planning guide: https://www.taxstrategyplaybook.com/newsletter
And before you go, send this to one more person in your circle who owns real estate or a business — a rumor is only expensive until somebody sends them the truth.
Contact David directly to discuss your situation or to receivee a free preliminary analysis of your property at David.wiener@cashflowwstrategies.us
#CostSegregation #RealEstateInvesting #TaxStrategy #BonusDepreciation #ShortTermRentals