If Your STR Manager Can’t Answer These 7 Questions, You Have a Problem

Most short-term rental owners don’t realize there’s a problem with their manager until revenue stalls, reviews dip, or something goes wrong.

By then, the damage is already done.

That’s why asking the right short-term rental manager questions early matters more than most owners realize.

A good STR manager should be able to answer specific questions about your property without dodging, generalizing, or blaming “the market.”

If you’re not getting clear answers to the questions below, it’s a red flag — not a personality issue, not “being picky,” and not you asking for too much.

Below are the 7 short-term rental manager questions every owner should be able to ask — and get real answers to.

1. What Is My Property Actually Earning — and How Does That Compare to Its Potential?

One of the most important short-term rental manager questions is about performance relative to potential — not just surface-level numbers.

If your manager only reports:

Occupancy
Gross revenue
“You’re doing fine compared to last year”

…that’s not transparency.

You should clearly understand:

How your revenue compares to similar nearby properties
Whether your STR is underperforming, meeting expectations, or leaving money on the table
What realistic upside exists based on market data

📊 Tools like AirDNA and PriceLabs are commonly used to benchmark true earning potential.

👉 https://www.airdna.co

👉 https://hello.pricelabs.co

2. What Specific Actions Are You Taking to Increase Revenue This Quarter?

Strong short-term rental managers are proactive, not reactive.

A good answer includes:

Adjusting minimum stays to capture orphan nights
Shifting pricing strategies for shoulder season
Testing amenity upgrades with ROI in mind

Weak answers include:

“We adjust pricing automatically.”
“The algorithm handles it.”
“The market is soft right now.”

Markets change. Strategy should change with them.

3. How Do You Decide Which Amenities Are Worth Investing In?

Not all amenities increase revenue — some just look good in photos.

One of the most overlooked short-term rental manager questions is why certain upgrades are recommended.

Your manager should explain:

Which amenities drive bookings in your specific market
Which increase ADR vs. just occupancy
How long it takes to see a return

At Oasis Escapes, we don’t recommend amenities unless we can clearly explain how they support revenue performance.

🔗 Internal link suggestion:

Related: How Amenities Impact STR Revenue (your future blog or services page)

4. How Quickly Are Issues Handled When Something Goes Wrong?

Problems will happen — that’s part of short-term rentals.

The real short-term rental manager question is:

How fast is the response?
Who handles it?
How are you kept informed?

If you’re finding out about guest issues after the stay, that’s reactive management — not hands-off ownership.

5. How Do You Protect My Home From Bad Guests?

If your manager says:

“Airbnb handles that,” or
“We’ve never had issues”

That’s a red flag.

A professional answer includes:

Guest screening standards
Minimum age policies
Monitoring high-risk booking patterns
Strategies for party-prone dates

According to Airbnb’s own hosting standards, prevention is more effective than cleanup.

👉 https://www.airbnb.com/help/article/3345

6. What Metrics Do You Track Beyond Occupancy and Revenue?

Occupancy alone doesn’t equal success.

Experienced managers track:

ADR trends
Booking window shifts
Review sentiment patterns
Guest complaints that signal operational issues

If your reporting stops at revenue totals, you’re missing the why behind performance.

7. If This Were Your Property, What Would You Change?

This is one of the most revealing short-term rental manager questions you can ask.

A strong manager will suggest:

Pricing refinements
Amenity improvements
Policy adjustments
Operational upgrades

If the answer is:

“Nothing — it’s perfect,” or
“That’s up to you”

You’re not getting strategic management — you’re getting coordination.

Why Asking the Right Short-Term Rental Manager Questions Matters

Most owners aren’t upset because of one big mistake.

They’re frustrated because:

No one explains why performance looks the way it does
Decisions feel reactive instead of intentional
There’s no clear improvement roadmap

That’s exactly why Oasis Escapes was built differently.

We believe transparency isn’t optional — and treating a property like our own means asking better questions and answering them honestly.

Learn more: Oasis Escapes Co-Hosting & Revenue Strategy

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