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Hey Smart Host and Sesemi Subscriber,

Here’s some big news out of D.C. that could supercharge your tax savings and unlock new opportunities in your short-term rental strategy…the Clock Is Ticking…⏳

The House already passed the bill on May 22 (215–214 vote)—it’s now heading to the Senate. While nothing’s guaranteed, savvy investors are already preparing in case it clears.

Pro tip: Don’t wait until it passes. If it goes through, you’ll want your improvements or purchases ready to deduct in 2025.

Hosted by OR & CA RE Broker and NMLS Mortgage Broker Anthony AJ Wong.

🧠 What Is the STR Tax Loophole?

The STR tax loophole allows W-2 wage earners and other high-income individuals to use real estate losses from a short-term rental against their active incomewithout qualifying as a real estate professional (REP) under IRS rules.

Key Requirements:

  1. Rental period must average less than 7 days OR less than 30 days with substantial services (like cleaning, guest communication, etc.).

  2. Material participation is required. You must be actively involved in the STR’s operations (typically ≥100 hours/year, and more than anyone else).

  3. The STR must not be rented to long-term tenants.

  4. You must own the STR personally (not just through an LLC unless it's a pass-through).

If these are met, losses from your STR become “non-passive”—meaning they can offset active W-2 income, potentially creating a massive tax deduction.

Enter 100% Bonus Depreciation (If Passed for 2025)

Bonus depreciation allows you to immediately deduct the entire cost of certain assets—like furniture, appliances, and even parts of the building structure (via a cost segregation study)—in the year of purchase or improvement.

As of now, bonus depreciation is 40% in 2025 and phasing out by 2027. The proposed legislation would restore it to 100% retroactively to January 1, 2025.

📉 Real-Life Example: $1M STR Purchase | $350K+ Wage Earner

Let’s say you buy a $1,000,000 STR property in 2025. Here’s how the numbers could break down:

Property Details:

  • Purchase Price: $1,000,000

  • Land Value (non-depreciable): $200,000

  • Building Value: $800,000

  • You perform a cost segregation study, which identifies ~30% of the building as eligible for bonus depreciation.

Depreciation Breakdown:

  • 30% of $800K = $240,000 eligible for immediate bonus depreciation

  • Add furnishings, appliances, startup costs: ~$20,000

  • Total write-off in Year 1 = $260,000

Tax Impact:

  • Your W-2 income: $350,000

  • You materially participate in the STR and meet IRS requirements

  • You apply the $260,000 deduction against your active income

Result:

  • Taxable income drops to ~$90,000

  • At a 35% marginal tax bracket (federal + state), that’s $91,000+ in tax savings

Bonus Tip: Stack with Other Strategies
  • STR + 100% Bonus Depreciation = huge year-one deductions

  • Add cost segregation studies to increase the amount eligible

  • Use Section 1031 exchanges in the future to defer gains on sales

📝 Final Notes

  • Always consult a tax professional familiar with STRs, cost segregation, and depreciation rules.

  • This strategy works best when:

    • You earn high active income (like W-2)

    • You can materially participate in the STR

    • You’re buying and/or improving an STR in a qualifying market

🔍 Why This Matters for Hosts & Investors

Whether you’re just starting out or scaling up, this kind of policy can significantly lower your tax liability and boost your ROI.

New hosts: Use it to offset startup costs fast
Seasoned operators: Upgrade your properties and deduct it all
Looking to expand? This makes the math work on deals that didn’t pencil before

Previously marginal investments? Now profitable.

This combo can help offset not just rental income—but even W-2 income for qualified hosts. But it’s not a DIY move. Talk to a tax pro who knows short-term rentals. Save time and focus on qualified prospects with our STR formula.

Check out our STR sales and most recent client testimonial:

🔐 Here are 10 Oregon Coast Vacation Rentals For Sale:

  • 436 S Franklin St Seaside OR - 2/1 1053SF - Verified STR eligible subject to parking and landscaping inspection. Asking $469,000

  • 29049 Vizcaino Ct Gold Beach OR - 3/2 1605SF - Turn-Key active STR detached townhome. Asking $545,000

  • 269 NE Williams Ave Depoe Bay OR - 2/2 1268SF - Turn-key STR newer construction Townhome. Asking $549,900

  • 4922 Oceana Dr Florence OR - 3/3 2440SF - Large home eligible for STR usages. Asking $720,000

  • 438 Buena Vista Loop Brookings OR - Oceanview STR eligible. Asking $789,000

  • 48450 Proposal Rock Loop - 4/4 2254SF - Active North Coast STR with creek frontage. Asking $800,000

  • 24880 E Arrah Wanna Blvd Welches OR - 3/2 339SF - Near Mt Hood with room for ADU. Asking $945,000

  • 33310 Cape Kiwanda Dr Pacific City OR - 5/3 4578SF- Commercial + STR. Asking $1,095,000

  • 5816 Martin Rd Florence OR - 4/5 3132SF - Lakefront Home with private dock. Asking $1.5M

  • 1021 S Prom Seaside OR - 5/4 4532SF - ‘Oceanfront’ large active STR. Asking $2.5M

BONUS: Here are two multi family listings

205 N Empire Blvd Coos Bay OR - Coastal Six Plex. Asking $645,000.

1560 S Downing St Seaside OR - Coastal Four-Plex. Asking $649,900.

👁‍🗨 Our exclusive STR HOT SHEET is updated daily and features 100+ active and off market vacation rental properties for sale. Search 24/7/365 at www.sesemisheet.com Text 541-800-0455 for the secret pass code!

Thank you for reading this week’s edition of Sesemi STReet your premier information source for vacation Rental and investment property insight throughout Oregon & California.

Browse ALL active and eligible Oregon Coast vacation rentals listed for sale on our invite only STR HOT website SESEMI SHEET updated daily! Text for secret passcode.

Selling a property sometime soon? Supercharge your 1031 exchange search with HIGH ROI properties including: Apartment Complexes, RV & Mobile Parks, Storage, Industrial, Commercial and Development Opportunities.

P.S. As a licensed NMLS mortgage broker with C2 Financial we cohesively support investors with curated loan programs. If you are in contract or considering an offer on a property nationwide, feel free to forward your BEST quote to our team for a zero obligation second look loan review. For those pending, we offer a 24 hour full loan commitment to help you and your agent win the offer! Reach out for optimized weekend Pre Approvals and professional mortgage support.

Ask about our premier mortgage programs:

  • Elite Jumbo & Super Jumbo Loan Rates

  • FHA, VA & Conventional

  • STR and AirBNB Mortgages

  • 1-100 Units + Commercial

  • Expedited refinances and HELOCS

  • DSCR (Debt Service Coverage Ratio) Mortgages for 1-100+ Units

  • Ground Up Construction financing

  • Alternative income verification (1099, Bank Statement, Asset depletion)

  • Private & Portfolio Programs

Anthony AJ Wong
Licensed Oregon Real Estate Broker
Fathom Realty Oregon
📞 541-800-0455 | License #201231202
🌐 My Website | 👖Bigger Pockets Feature Agent Profile | 🗓️Book 15 Minute STR Consultation
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FL NMLS ID: 2297941

Weekly curated list of the HOTTEST luxury vacation rental properties on market.

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