Seeking Advice on Transitioning from Owner-Occupied B&B to Full Short-Term Rental

Lance166
Level 2
Dundee, OR

Seeking Advice on Transitioning from Owner-Occupied B&B to Full Short-Term Rental

Hello Airbnb community!

I’m considering transitioning my current owner-occupied Bed and Breakfast (3 bed, 2 bath) to a full Short-Term Rental operation by renting out my entire property as a 5 bed, 3 bath home. I’d love to hear from anyone who has made a similar transition or has insights into the potential impacts and challenges.

Here are my main questions and concerns: Any help with items are appreciated!

  1. Property Taxes: Will changing from an owner-occupied B&B to a full short-term rental significantly increase my assessed property value or property tax rate?

  2. Tax Implications: How significant is the loss of primary residence tax benefits, such as the capital gains exclusion or homestead exemptions?

  3. Insurance Costs: What kind of increases should I expect in insurance costs when switching to a short-term rental policy? Any recommendations for good insurance providers that cater to short-term rentals?

  4. Business and Registration Costs: Beyond the initial registration fees and paperwork, are there any ongoing costs or surprise fees I should prepare for?

  5. Other Downsides: Are there any downsides I might not be considering, such as guest management issues, stricter regulations, or hidden operational challenges?

  6. Maximizing Revenue: For those of you who’ve increased your rental capacity, did the income from renting the entire property (vs. a portion) offset the additional costs and risks?

  7. Legal/Regulatory Considerations: Have you had issues with zoning, licensing, or other legal hurdles after making a similar change?

Any advice, resources, or personal experiences you can share would be incredibly helpful. Thank you so much for your time and expertise!

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