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June 17, 2025 31 mins
In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere, CPA, put ChatGPT to the test to answer a question that’s on the minds of many real estate investors: Can AI actually replace your tax advisor? Key topics covered: - Where AI like ChatGPT performs well and where it fails - Real-time testing of ChatGPT on short-term rental strategies - Common AI mistakes on REPS, depreciation, and passive loss rules - A new listener question ChatGPT got both right and wrong - Why nuanced tax strategy still requires a real human advisor - How IRS regulations trip up AI systems - Real examples where relying on ChatGPT could lead to audit risk Plus, Thomas shares a fresh, real-world test he ran through ChatGPT just hours after recording and breaks down exactly where it gave conflicting answers. If you’re using AI to guide your tax decisions, this is an episode you don’t want to miss. 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: go.therealestatecpa.com/41JuQBX The Tax Smart Real Estate Investors podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests.
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