Tax Loss Harvesting Strategies

In this episode of the Tax Smart REI Podcast, Thomas Castelli and Justin Shore discuss essential year-end tax strategies for real estate investors looking to close out 2025 strong. As Q4 winds down, they walk through the most effective levers you can pull before December 31 to minimize taxes, maximize deductions, and set yourself up for a smoother filing season. From vehicle deductions and short-term rental timing to real estate professional status, cost segregation, and the latest SALT deduction updates, Thomas and Justin share practical insights for both active and passive investors. They also highlight common pitfalls, like letting the tax tail wag the dog, and explain how to apply these strategies correctly in your own situation. You’ll learn: - How to qualify for 100% bonus depreciation on vehicles and real estate in 2025 - What it really takes to lock in short-term rental tax benefits before year-end - Why REPS qualification is nearly impossible to start from scratch in Q4 - When to complete a cost segregation study (and when it can wait) - How the updated SALT cap could impact your AGI and deductions - Key deadlines for 401(k)s, IRAs, HSAs, and paying your kids through your business - Why bookkeeping and documentation now will save you headaches in tax season Whether you’re a seasoned investor or just looking to make smart year-end moves, this episode breaks down the most valuable tax strategies for real estate professionals, with clear guidance on how to apply them responsibly and in compliance with the IRS. 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. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.