What Are Some Commonly Overlooked Mistakes in Running a Short-Term Rental?

Question

Hey everyone!

I’m currently diving deeper into the world of short-term rentals, and I’ve been learning a ton—but I know there are always those little details that can make or break a guest experience or hurt profitability without even realizing it.

So I wanted to ask:
What are some mistakes you’ve seen (or made!) when operating a short-term rental that tend to get overlooked?

Could be anything—

• Pricing strategy issues
• Guest communication slip-ups
• Design/staging oversights
• Maintenance scheduling
• Legal/regulatory blind spots
• Anything you wish you knew earlier

Pricing strategy issues

Guest communication slip-ups

Design/staging oversights

Maintenance scheduling

Legal/regulatory blind spots

Anything you wish you knew earlier

Looking to learn from the community here—your insight could save someone a big headache down the line (including me). Appreciate any thoughts you’re willing to share!

Thanks in advance!

John Underwood · Answer

Make sure you have everything in your house. Checklists are great, but best way is to stay in your house for a couple days. You will quickly see what is missing or what needs some attention.

Collin Hays · Answer

The most overlooked mistake is lack of attention to risk management, and it can get you into a boatload of trouble. Providing a continuously safe place for guests should be your highest priority, because laziness in doing so can turn into your greatest liability.

Of course, having a liability insurance policy suitable to your risk - running a small hotel - is part of the solution. That policy will provide benefits for guest death and injury, provided you as the owner were not grossly negligent in providing a safe accommodation. "Gross negligence" is the insurance company's escape hatch. If that line is crossed, you are now the insurance company.

What is gross negligence?  My handy AI Chat says "Gross negligence refers to an act showing a severe and reckless disregard for the lives or safety of another person. It involves a conscious and voluntary disregard of the need to use reasonable care, likely to cause foreseeable grave injury or harm to persons, property, or both."- That wasp nest perched above your doorstep that you ignored.

- The rickety steps you decided to wait until next year to place, like you did last year.

- The tree swing that you mounted one summer for the kids, and the rope is now about to break.

- That door switch in the bedroom that you've notice has always been curiously hot.

I mention each of these things, because I am aware of claims - and settlements - related to each of them, two of them my own homeowners, that have occurred over the last 20 years. We have also actually fired two homeowner clients because of their lack of willingness to repair items that we felt were unsafe.

If you are going to self-manage, then self-manage, including periodic comprehensive safety inspections, and making necessary repairs. Your net worth depends on it.

Renee Krystek · Answer

Great question! One often-overlooked design mistake I see (and have experienced as a visitor) is designing for photos instead of function. A place might look amazing in listing photos with bold accent walls and trendy furniture but once a guest arrives, they realize there’s no spot to put a suitcase, not enough lighting to read in bed, or nowhere comfortable to sit and relax.A lot of this can be solved by the suggestions above from  & @John Underwood & @Mike Grudzien.

Think like a guest. Where do they drop keys? Charge phones? Set down toiletries? Design for those moments.

Invest in durable, cleanable materials. That white boucle chair might look great until it’s had three guests and a spilled latte.

Don’t overlook lighting. Layered lighting (ambient + task) makes the space feel welcoming and usable at all hours.

Also in the beginning, whether you are installing or contracting it out... you will produce SO MUCH trash/recycling (imagine every item comes in some sort of box with wrapping). You may want to plan for your own dumpster pickup.

James Carlson · Answer

Nothing crazy different here:

-- Know the Airbnb laws/HOA rules around STRs. And any short-term rental regulations in the works. So work with an agent that knows STR laws. (Shameless plug: Like an agent like me in Colorado that follows Airbnb rules.)

-- Don't skimp on design and furniture. The STR world is competitive. If you're buying at today's prices at today's rates, you've got to stand out.

-- Same for amenities. Hot tubs, saunas, game rooms, star-gazing domes, whatever ... you need to stand out.

-- When you find a good cleaner, pay them well to keep them. It is worth it.

Mike Grudzien · Answer

John is spot on.  I have worked with over 700 new Hosts.  I tell everyone that once they think they're set up, stay in the property for a day or two.  Have a notebook with you to write down every time that you are reaching for something and it isn't there.

Jennifer Green · Answer

Pricing is crucial; I switched to Pricelabs, which adjusts prices daily for my market. My revenue has consistently increased by 35% over the last six months.

I have all hardwood floors, walls, and leather furniture, which makes it easier to clean and does not absorb odors.

Also, I list places out of the regular tourist stuff into categories like date night, fun for kids, and adults, etc. We get a lot of positive feedback, and guests usually plan a return trip just to do the other stuff or to bring their family out next time. We have held consistently with a 30 to 50% guest return rate, which has helped us tremendously during the slow times.

Ryan Coon · Answer

Hi @Sage Bertran, Congrats on diving into the world of STRs. Perhaps this isn't exactly what you're looking for, but one thing I often see overlooked on the frontend is confirming that you are buying in a jurisdiction and community that allows short term rental. I've seen unfortunately far too many investors, especially those new to STRs, who purchase a property with the intent of using it as an STR only to find out after closing that STR's are not allowed by local ordinance, HOA rules, etc. There is no quicker way to have your investment plans derailed than to find out that the planned activity is not allowed.

Thus, as a takeaway, especially with STRs it is very important to thoroughly research the market you are buying into (e.g. the city, county, etc.) including both local ordinances and zoning laws, and also read through any HOA documents such as the CC&R's and rules to make sure you are not prevented from using the property as an STR before you purchase.

Note: This information is for
educational and informational purposes only and does not constitute legal,
tax, or financial advice. No attorney-client, fiduciary, or professional
relationship is established through this communication.

Krishnan Iyer · Answer

- All about Real Estate/STR taxes (State, Federal, Occupancy Tax etc.)- Material Participation- Cost Segregation/Bonus Depreciation

Krishnan.

Andrew Steffens · Answer

I see you tagged Orlando is that your desired market?  If so, fair warning, it is extremely saturated.  Out of your list, pricing will be key.  That market is a race to the bottom, so if you are not competitively priced you will not get bookings.

What Are Some Commonly Overlooked Mistakes in Running a Short-Term Rental?

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