2026 Hilton Head Investor Hub: Cost Segregation, STR Loophole & Tax Strategy Guides

"2026 Hilton Head Investor Tax Advantage Series

# Cost Segregation & STR Loophole Hub for Hilton Head Investors

This page brings together all of my 2026 guides on cost segregation, the STR loophole, and real-world case studies for Hilton Head and Bluffton investment properties. If you're a short-term rental owner, high-income earner, or investor planning a coastal purchase, start here.

Use this hub to move through the series in order, jump straight to the calculator, or share it with your CPA and lender.

Part 1: The 2026 Hilton Head Guide to Cost Segregation

Learn what cost segregation is, why it’s an IRS-approved strategy, and how a $400,000 Hilton Head rental can legally generate nearly $70,000 in first-year depreciation. This is your foundation for everything else in the series.

👉 [Read Part 1: Cost Segregation 101 for Hilton Head Investors →]()

Part 2: The STR Loophole – Why Hilton Head Short-Term Rentals Get Extra Tax Benefits

Discover how the STR loophole works, what the IRS considers a short-term rental, and how Hilton Head owners can use STR non-passive status to offset W-2 and active income. This is essential if you’re using Airbnb/VRBO as part of your tax strategy.

👉 [Read Part 2: STR Loophole & Material Participation →]()

Part 3: Case Studies – $400K, $750K & $1.2M Hilton Head Properties Compared

See side-by-side examples of how cost segregation performs at three real-world price points. Understand how first-year depreciation, tax savings, and ROI change as you move from condos to luxury STRs with pools and ocean proximity.

👉 [Read Part 3: 2026 Hilton Head Cost Segregation Case Studies →]()

Part 4: How to Qualify for STR Non-Passive Status or Real Estate Professional Status (REPS) in 2026

Learn the differences between STR non-passive status and Real Estate Professional Status, who each is best for, and how they can unlock the ability to use cost segregation to offset W-2 and other active income.

👉 [Read Part 4: STR Non-Passive vs Real Estate Professional Status →]()

Interactive Tool: 2026 Cost Segregation Calculator for Hilton Head

Ready to see how the numbers might look on your own property? Use the interactive calculator to estimate depreciable basis, bonus depreciation, total first-year deductions, and potential tax savings for any price point.

👉 [Use the 2026 Cost Segregation Calculator →]()

Downloadable Guide (Optional): 2026 Hilton Head Investor Tax Advantage Playbook

Turn this series into a shareable, printable playbook that you can review with your CPA, lender, or investing partners. The PDF version walks through the same concepts with consolidated examples and checklists.

👉 [Get the PDF: 2026 Hilton Head Investor Tax Advantage Playbook →]()

Who This Series Is Designed For

This hub is built for:

• Short-term rental (STR) owners in Hilton Head, Bluffton, and the Lowcountry
• High-income W-2 earners looking for legal tax strategies
• Real estate investors comparing different price tiers and property types
• Second-home owners considering renting their property part-time
• CPAs, lenders, and advisors working with coastal real estate investors

If you’re planning to buy, sell, or scale a Hilton Head STR portfolio, this series gives you the language, examples, and frameworks to have smarter conversations with your tax and finance team.

Want a Property-Specific Cost Seg & STR Tax Strategy?

I help investors analyze real Hilton Head and Bluffton properties using income projections, cost segregation estimates, STR tax strategies, and long-term scaling plans.

👉 I can run a custom analysis for your next purchase—or your current portfolio.[Request Your Custom STR & Cost Seg Review →]()

About the Author

By: Donna Gilmore – Realtor & Director of Operations for the #1 eXp Team in South Carolina

Expert Real Estate Mentor & Team Transition Specialist | AI Systems Strategist for Top-Producing Agents & Teams | Creator of the Systems-to-Scale AI Implementation Method™

Helping agents, teams, and investors implement AI, automation, and high-performance systems to grow smarter, scale faster, and dominate their markets.

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