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Tax Strategies NO ONE is Talking About

In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa break down under-the-radar tax strategies real estate investors and high earners can use to cut their tax bills—plus the mistakes that quietly cost people thousands. You’ll learn: How land banking works, who it fits best, and why it can be a powerful long-term tax play The advanced “1031” strategies including reverse and improvement exchanges to defer taxes while upgrading properties Niche but huge deductions like solar (only if you own the panels) and casualty losses Two common pitfalls: accidentally triggering the 3.8% NIIT and missing the §469 grouping election that can trap losses. Request a FREE 30-Minute Discovery Meeting: https://go.therealestatecpa.com/44I5EwK Subscribe to REI Daily & Enter to Win a FREE Strategy Call: https://go.therealestatecpa.com/41InoXP 0:00 Intro – Tax Smart REI Podcast 0:05 Episode overview: “outside-the-box” strategies 0:41 Sponsor: Hall CPA year-round tax planning 1:21 Land Banking: what it is + who it’s for 2:32 Why land banking can mean capital gains vs ordinary tax 3:24 Developer play: related-party sale + S-corp development strategy 5:28 Example walkthrough: hold vs develop vs sell to S-corp 8:14 IRS scrutiny + “Winthrop factors” caution 9:02 Advanced 1031s: reverse & improvement exchanges 9:14 Reverse 1031 explained (buy first, sell later) 10:37 Reverse 1031 risks: costs, deadlines, what if it fails? 13:27 Improvement 1031 explained (use exchange to build/improve) 14:20 Key rule: you can’t already own the land 14:38 Biggest challenge: construction timeline within 180 days 15:24 Sponsor: Engineer Tax Services (cost segregation) 17:35 Casualty losses: what they are + who should consider them 18:00 Business vs personal casualty loss differences 18:45 Disaster declarations (state vs federal) + why it matters 20:17 Example: insurance proceeds vs loss calculation 21:15 Are casualty losses ordinary deductions? (Yes) 21:37 What if you rebuild instead of walk away? 22:22 Solar deductions: what investors need to know 23:04 Solar = tax credit + deduction (bonus/179) 23:34 Timing window: solar credit ending soon (per “Big Beautiful Bill”) 24:03 Mistakes to avoid: NIIT (3.8%) 24:32 NIIT mistake: REPS box not checked (real example: ~$1M paid) 26:21 REPS benefit for full-time real estate investors (NIIT + losses) 27:42 469-9 grouping election explained (1.469-9(g)) 28:41 Common mistake: not filing election + late election limitations 29:36 Best practice: file grouping election every year 30:24 When not grouping can make sense (unique case) 31:21 Final advice: review returns, ask questions before filing 32:11 Outro + year-end checklist + announcement next week 33:01 Disclaimer 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.