354. Can Property Management Kill Your STR Loophole? (And Other Costly Mistakes)
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Nov 19, 2025
Explore why depreciation is crucial for rental properties and how property management can sabotage your short-term rental strategy. Discover the complexities of bonus depreciation cuts and what documents you need for tax strategies. Learn how to classify short-term rental hours toward professional status and avoid costly mistakes with syndication losses. Get valuable year-end action items, from time logs to charitable contributions, to position yourself for success before the deadline.
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volunteer_activism ADVICE
Always Take Rental Depreciation
Take depreciation on rental properties; you must claim it when the property is rented and placed in service.
Replace a preparer who refuses, because failing to depreciate is incorrect and creates future issues.
volunteer_activism ADVICE
Cost Segregation Can Wait Until Filing
You do not need a cost segregation study completed by year-end to apply it to a 2025 purchase.
Get the report to your preparer before you file (ideally before April 15) so it can be applied to your return.
insights INSIGHT
2025's January Cutoff Matters
A unique 2025 timing rule creates a January 19 cutoff that can limit you to 40% bonus depreciation.
Contract facts and construction spending before that date determine whether you get 40% or 100% bonus depreciation.
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In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa field real questions from the Tax Smart Investors Facebook group, their online community, and recent client conversations to tackle the most common and most confusing year-end tax issues real estate investors are facing.
You’ll learn:
- Why you must take depreciation on your rental properties
- When you’re stuck with 40% vs 100% bonus depreciation
- How short-term rental hours do (and don’t) count toward real estate professional status
- When using a property manager or a seller staying in the property after closing can blow up your short-term rental strategy
- The tests you need to meet if you want syndication losses to be non-passive
- Why condos still need a land allocation for depreciation even if you “don’t own the dirt”
Practical year-end action items: time logs, charitable bunching, retirement contributions, and how to use the free Year-End Tax Checklist without panic-buying a bad deal for a one-year tax win
Whether you’re trying to squeeze in a year-end short-term rental, line up a cost seg study, or simply avoid costly mistakes on your 2025 return, this episode will help you zoom out, think long term, and decide which moves are truly worth making before December 31st — and which ones can wait.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Subscribe to REI Daily & Enter to Win a FREE Strategy Call:
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Connect with Engineered Tax Services:
https://portal.engineeredtaxservices.com/cost-segregation/quick-start?utm_source=Live+Event&utm_medium=Others&utm_campaign=hall_cpa&pagesense_source=729733000061045013&utm_term=kim_lochridge&utm_content=cost_segregation
Get the Year-End Tax Checklist:
https://go.therealestatecpa.com/4pj63id
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