Everything We Researched Before Closing on Our Airbnb

ByTanyaPetersonRealtor

By the time we found the house that would eventually become The Cabin on the Canal, we were excited.

Really excited.

But excitement can get buyers into trouble.

As a Realtor, I’ve seen people fall in love with properties, overlook important details, and spend years regretting decisions they made too quickly. I didn’t want that to happen to us.

Buying a short-term rental is very different from buying a primary residence.

You’re not just purchasing a property.

You’re purchasing a business, a lifestyle, and a long-term investment.

That meant we had homework to do.

A lot of homework.

Could We Even Use It as a Short-Term Rental?

Before buying a vacation rental, understanding local regulations is the first step.

This was our biggest question from the beginning.

Before falling in love with any property, we needed to know whether our plans were even possible.

Many cities and counties have short-term rental restrictions. Some require permits. Some limit the number of rental nights. Some have waiting lists. Others prohibit vacation rentals altogether.

We didn’t want to discover after closing that our dream property couldn’t operate the way we intended.

Fortunately, The Cabin on the Canal is located in the Three Rivers area of Deschutes County, outside the City of Bend, which provided a major advantage.

But we weren’t interested in assumptions.

We wanted facts.

So we started digging.

Insurance Was a Bigger Deal Than I Expected

Photo by Zulfugar Karimov: https://www.pexels.com/photo/close-up-of-metal-keys-on-marble-surface-37003193/

Insurance was one of the biggest surprises in our buying journey.

Like many people, I started with the company I normally use for my own insurance. We secured what we thought was coverage and checked that item off our list.

Or so I thought.

About a month later, we discovered we didn’t actually have coverage.

The issue wasn’t the hot tub.

It wasn’t the dock.

It wasn’t even the fact that the property would operate as a short-term rental.

It was the wood stove.

Apparently, many insurance companies view wood-burning stoves in vacation rentals as an increased risk because of fire concerns and liability exposure.

Honestly, that never crossed my mind.

I had considered the obvious questions:

Would the property be insurable as a rental?

Would the hot tub require additional coverage?

Would the water access create liability concerns?

But a wood stove?

That caught me completely off guard.

Suddenly, we were searching for another insurance provider willing to cover the property.

That wasn’t on my checklist.

And it certainly wasn’t something I expected after thinking we already had insurance secured.

Lesson learned:

Never assume you have insurance until you have the actual policy in place and understand exactly what is—and isn’t—covered.

Ask Questions About Unique Features

One thing we quickly learned is that the features that make a property special are often the same features insurance companies evaluate differently.

If your potential vacation rental includes any of these, ask detailed questions before closing:

  • Wood stoves
  • Hot tubs
  • Water access
  • Docks
  • Recreational equipment
  • Detached structures
  • Multiple owners
  • Unique amenities

The things that make guests excited about a property can also create additional responsibilities for owners.

Utilities Matter More Than You Think

Photo by Matthew DeVries: https://www.pexels.com/photo/brown-wooden-house-on-snow-covered-ground-3773244/

Guests don’t care whether you’re on septic.

They don’t care if you have a private water system.

They don’t care about your garbage schedule.

They simply expect everything to work.

Before closing, we wanted to understand:

  • Septic systems
  • Water sources
  • Internet availability
  • HVAC systems
  • Garbage service
  • Snow removal
  • Maintenance requirements

Because when guests arrive, they don’t want explanations.

They want a great experience.

We Thought About Future Resale

One thing Realtors naturally do is think ahead.

Even before purchasing, we asked ourselves:

  • What happens if short-term rental regulations change?
  • What if we decide to stop hosting?
  • Would this property appeal to traditional buyers?
  • Could it become a long-term rental?
  • Would future owners appreciate the same features we did?

The answer was yes.

That gave us confidence.

We weren’t just buying a vacation rental.

We were buying a property with options.

Guest Experience Started Before We Owned It

Photo by Wolf Art: https://www.pexels.com/photo/set-glass-dining-table-20130520/

Even before closing, I was already thinking like a host.

Instead of only asking, “Do we love this house?”

I started asking:

“Will our guests love this house?”

Could ten people comfortably gather?

Was there enough parking?

Would families enjoy staying here?

Were there enough bathrooms?

Would guests have privacy?

Could people work remotely?

Would dogs be safe and comfortable?

Those questions became just as important as square footage, finishes, and design.

I Became a Little Obsessed

I’ll admit it.

Once we went under contract, I became a research machine.

I watched YouTube videos.

I joined Facebook groups.

I listened to podcasts.

I read articles.

I searched forums.

Some information was incredibly helpful.

Some information was questionable.

And some information simply left me with more questions.

Everyone had opinions.

But what I couldn’t find was a true roadmap.

Most people shared the success stories.

Very few talked about the mistakes.

I wanted both.

I wanted to know what could go wrong before it happened.

Learning From Others Saved Us

One of the biggest lessons I learned was that you don’t have to reinvent the wheel.

There are hosts who have already made the mistakes.

There are owners who have already solved the problems.

There are systems that work.

And there are expensive lessons you can avoid simply by asking the right questions.

I became a sponge.

And honestly, I’m still learning every day.

We Knew There Would Be Surprises

No amount of research eliminates every surprise.

That’s part of ownership.

Things break.

Plans change.

Budgets stretch.

Projects take longer than expected.

That’s reality.

But by doing our homework before closing, we felt prepared.

Not perfect.

Just prepared.

And sometimes, that’s the best you can hope for.

Lessons Learned

Looking back, these were some of our biggest takeaways:

  • Excitement should never replace due diligence.
  • Research regulations before falling in love with a property.
  • Insurance deserves far more attention than most buyers give it.
  • Think about resale before you buy.
  • Learn from people who have already made mistakes.
  • Never assume insurance is finalized until you have the actual policy.
  • The features that make a property unique can also create additional challenges.

A Realtor’s Perspective

I’ve always told my clients that buying real estate requires both emotion and logic.

Too much emotion can lead to rushed decisions.

Too much logic can cause you to miss opportunities.

The key is balance.

Thankfully, we took the time to ask questions before closing instead of after.

And looking back, that research gave us the confidence to move forward.

What’s Next?

In the next blog, I’ll share what we inherited when we officially took ownership—and why vacation homes aren’t always as “move-in ready” as they appear.

Thinking About Buying a Short-Term Rental?

As both a Realtor and a host, I’d love to help you navigate the process and avoid some of the expensive mistakes we uncovered along the way.

Ready to Experience The Cabin on the Canal?

Come enjoy everything Central Oregon has to offer and discover why we fell in love with this special place. The Cabin on the Canal

Follow Along

This post is part of the Building the Cabin on the Canal series, where I’m sharing the real lessons we’ve learned—from purchasing the property and preparing it for guests to everything that comes with owning a vacation rental.


Tanya Peterson, Principal Real Estate Broker
Next Level Real Estate PNW | John L. Scott Market Center
503-260-2164 OR Lic #200407018
ABR ~ CRS ~ GRI ~ e-Pro ~ SRES
#TanyaPetersonRealEstate #NextLevelRealEstatePNW
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