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AJ Wong
  • Real Estate Broker
  • Oregon & California
683
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818
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The time to Shop for a Vacation Rental and the 2026 STR Loophole is...Now-ish

AJ Wong
  • Real Estate Broker
  • Oregon & California
Posted

With taxes in the rear view, the time for investors to plan for next year and begin actively shopping for their next short-term rental investment has arrived. How do we know? Each year of the past five we've sold more STRs than the year before..here's the real world acquisition timeline: 

Consider that for investors that are 'peddle to the floor' and just initiating their investment search - prospecting is complete by June/July. Closing by July/August and permitting/licensing, furnishing and launching August/September. That provides October, November and December to qualify, operate and leave room for the inevitable delay or failed transaction. 

Typical STR Timeline:

30-60 Days | Shopping & Tours

30-45 Days | Closing

30-60 Days | Permit, Design, Furnish

LAUNCH! 

Investors should keep in mind that prime STR prospects will likely see even greater demand as the year progresses and should anticipate competition. Limited inventory could delay or extend the shopping/closing timeline. Leave margin for error.

One asterisk is that investors could reduce the permit, design, furnishing period (extending their search period) by focusing on a turn-key or active vacation rental. If the eventual plans include revitalization or additional amenities technically those capital improvements could be pushed out to the next year - although it won't count towards the investment for that year. In other words - a prospect that requires a sauna or new flooring in the bedrooms to be 'optimized' could be launched 'as-is' to qualify. This strategy is not ideal for full tax incentives but could fill as a stop-gap rather than missing the bonus entirely. 

  • AJ Wong
  • 541-800-0455
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Mike Grudzien
#5 Short-Term & Vacation Rental Discussions Contributor
  • Lender
  • Eugene, OR
1,465
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2,214
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Mike Grudzien
#5 Short-Term & Vacation Rental Discussions Contributor
  • Lender
  • Eugene, OR
Replied

AJ,
Thanks for laying out a smart timeline.

  • Mike Grudzien
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