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The Money · 35 stories

The Money

Occupancy, rates, revenue, taxes, insurance, financing and what the numbers are really doing.

  1. The Money Renting to Film Crews Requires Massive Premium Pricing When location scouts offer triple your nightly rate, it sounds like easy money. The reality is a high-risk commercial operation that can wreck your pr By Dana WhitfieldSeptember 22, 2026Analysis
  2. The Money The Real Cost of Realtor.com's Secondary Market Predictions Realtor.com wants owners to buy into under-the-radar markets. But the operational reality of secondary-market hosting is a far cry from the portal's r By Dana WhitfieldSeptember 21, 2026
  3. The Money The Coastal Cool Down: What the Hilton Head Summer Showdown Means for Short Term Rentals New data from South Carolina's premier beach market reveals a stark shift in the battle for occupancy. As traditional resorts claw back market share, By Dana WhitfieldSeptember 18, 2026
  4. The Money Interest Rate Swaps Save Large Short Term Rental Portfolios From Insolvency While individual hosts struggle under the weight of rising mortgage rates, institutional operators are using sophisticated financial derivatives to fr By Dana WhitfieldSeptember 15, 2026Analysis
  5. The Money Costa Rica Short-Term Rentals Face Oversupply as Tourist Numbers Lag With active listings nearing 49,000 while international arrivals flatten, vacation rental hosts in Costa Rica are facing a brutal squeeze of high cost By Dana WhitfieldSeptember 14, 2026
  6. The Money The Secondary Debt Trap Gutting Vacation Rental Portfolios During the post-pandemic vacation rental rush, thousands of retail investors tapped their primary home equity to fund down payments. Now, the double-l By Dana WhitfieldSeptember 10, 2026Analysis
  7. The Money AirDNA's AI Gambit: Is The Data Kingpin About To Remake STR Pricing? The market intelligence giant just dropped 'Adapt,' an AI-native revenue management system. This isn't just another software launch. It's a shot acros By Dana WhitfieldSeptember 2, 2026
  8. The Money IDAHO SUPREME COURT SMASHES CITY'S STR BAN: A LANDMARK WIN FOR PROPERTY RIGHTS The highest court in Idaho just delivered a seismic blow to municipal overreach, striking down an outright ban on non-owner-occupied short-term rental By Dana WhitfieldAugust 22, 2026
  9. The Money Rhode Island’s 'Swift Tax' Lawsuit Ignites New Front in STR War A lawsuit over Rhode Island's so-called 'Taylor Swift Tax' is more than a local spat. It’s a chilling signal to every host and manager: cities are com By Dana WhitfieldAugust 22, 2026
  10. The Money INSURANCE BOMB DROPS: Your Airbnb Listing Just Canceled Your Homeowner's Policy The nightmare scenario for every short-term rental host is no longer a 'what if' but a brutal reality. Insurers are lurking, ready to deny claims when By Dana WhitfieldAugust 18, 2026
  11. The Money The Great Reset: Asking Prices Take Steepest Dive Since 2017 – What It Means for Your STR National asking prices have plunged, marking the sharpest annual decline in seven years. It sounds like opportunity, but a looming affordability crisi By Dana WhitfieldAugust 13, 2026
  12. The Money GUEST ACQUISITION COST IS THE SILENT KILLER OF HOST PROFITS Hosts obsess over occupancy and ADR, but the true cost of filling a night across platforms and direct channels remains an unquantified drain. It's tim By Dana WhitfieldAugust 7, 2026Analysis
  13. The Money The Seasonality Trap: How Idle Listings Turn Cash Flow into a Cliff Dive The off-season isn't just slow, it's a financial black hole if hosts aren't prepared. Learn to price smart, build reserves, and avoid the revenue cras By Dana WhitfieldAugust 6, 2026Analysis
  14. The Money Platform Addiction Is Bleeding You Dry: Direct Booking Is Your Only Escape For too long, hosts have surrendered their profits and their futures to the whims of the booking giants. It’s time to stare down the real cost of depe By Dana WhitfieldAugust 4, 2026Analysis
  15. The Money The Quiet Audit Trigger: STR Tax Moves That Draw IRS Fire Hosts chasing maximum deductions often flirt with danger. We break down the aggressive tax strategies that flag your short-term rental business for an By Dana WhitfieldAugust 4, 2026Analysis
  16. The Money Underwater and Overleveraged: The Great STR Reckoning Arrives For hosts who bought at peak prices with cheap money, the current market is a brutal reality check. We break down the stark choices: refinance, sell, By Dana WhitfieldJuly 22, 2026Analysis
  17. The Money TAX REVOLUTION: Your STR Just Got Reclassified Commercial and the Bill is Brutal The property tax hammer just dropped. Cities are reclassifying short-term rentals as commercial, triggering catastrophic new tax bills and upending ho By Dana WhitfieldJuly 22, 2026Analysis
  18. The Money Your ADR Is Lying To You: The Quiet Death Of Profitability That glowing Average Daily Rate on your dashboard? It's a seductive lie. It hides the relentless discounting and calendar chaos that's quietly drainin By Dana WhitfieldJuly 21, 2026Analysis
  19. The Money Cap Rates Don't Lie: The Brutal Truth of STR vs LTR Returns Forget the fantasy of passive income from nightly stays. STR NEWS pulls back the curtain on the hidden costs and real risks, forcing a hard look at ho By Dana WhitfieldJuly 21, 2026Analysis
  20. The Money THE RESERVE FUND: The Silent Killer Every Host Skips Until It's Too Late It's the financial boogeyman everyone knows exists but few prepare for. We're talking about the capital set aside for the inevitable, torrential downp By Dana WhitfieldJuly 21, 2026Analysis
  21. The Money SETUP SHOCK: THE HIDDEN FURNISHING BILL THAT CRUSHES STR PROFITS Many new short-term rental hosts see the promise of passive income. Few see the deep, swirling money pit of setup costs until it's too late. This is h By Dana WhitfieldJuly 21, 2026Analysis
  22. The Money The Silent Killer: Skyrocketing Insurance Premiums Are Drowning STR Profits It's not a market crash or a regulatory crackdown that's quietly gutting host profits. It's the silent, relentless creep of insurance costs, especiall By Dana WhitfieldJuly 20, 2026Analysis
  23. The Money Your Manager Is Bleeding You Dry: How to Spot the Sabotage The 20-to-30-percent question isn't just about the number; it's about what you truly get for it. STR NEWS exposes the signs your property manager is f By Dana WhitfieldJuly 20, 2026Analysis
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