Why the Reduction

Simply put, some of the properties weren’t performing to our expectations. While they were still profitable, the returns didn’t justify the time and effort required to manage them hands-on. So, we made some strategic decisions:

• Sold four properties to retail buyers

• Converted the other four into long-term rentals

• Kept two in our rental portfolio

• Sold two to investors wanting turnkey rentals

That left us with eight highly optimized short-term rentals that consistently exceed our financial projections every month.

The Slow Season is Coming

As we move into the slower season, we’re pivoting toward mid-term stays—guests who stay 30 days or longer. These bookings come from insurance carriers, relocation services, and construction crews working on local projects.

The numbers are strong: our monthly rates average $4,000+, and occupancy stays near 100%. The best part? No constant turnovers, no resupplies, and no added housekeeping costs. These properties practically run themselves—requiring only occasional guest communication and supply runs.

That is, until last week.

The Week of Chaos

The week of September 29 was a rough one. Here’s what went down:

Property #1 (Monday) – The Wasps
A guest reported wasps inside the home. After inspection, we discovered a nest in the attic. It wasn’t safe for the guest, so we allowed them to cancel their remaining stay. A three-month booking was cut down to just four weeks. Pest control took three days to resolve the issue and we relisted the property. Thankfully, we quickly secured four new bookings so we are on our way to recoup the lost revenue for October.

Property #2 (Tuesday) – The Rodents
Our departing mid-term guests of two months left the house in terrible condition—dirty, with food left out everywhere. Naturally, this attracted rodents. Fortunately, we had a three-day gap before the next check-in. We sealed all possible entry points and set traps and bait in the crawlspace. The issue seems resolved, but our housekeeper has a strong aversion to rodents and made it clear she won’t clean the house again if there’s any sign the problem persists. Fingers crossed it’s handled for good.

Property #3 (Tuesday) – The Fallen Tree
A tree fell in the front yard in the middle of the night—thankfully, the property was unoccupied and the tree landed harmlessly across the lawn. We had it removed the same day, but it cost $1,000.

Property #4 – (Wednesday) The Tree Limb Incident
On the final day of a four-day VRBO booking, a tree limb fell on a guest’s vehicle. Unfortunately, the guest didn’t purchase VRBO’s supplemental insurance. They’re now asking me to cover $2,600 in damages.

I explained that this was an “act of God,” as I had no prior knowledge the tree limb was dead or hazardous. Under the law, a property owner is only liable if they knew—or should have known—about the danger. I apologized sincerely and advised them to file a claim with their auto insurance. They still believe I’m responsible, but the law is clear. I had zero knowledge of any dead tree limbs prior to this incident.

Property #5 – (Friday) Worst Guest Ever
After nearly four years of hosting, I knew this day would come—but I still dreaded it. After a five day stay, the worst guest we’ve ever hosted finally checked out. They broke nearly every house rule: smoking indoors, bringing unauthorized guests and pets, violating quiet hours, and overstaying checkout by almost two hours—delaying housekeeping from cleaning and preparing for the next guest arriving later in the afternoon.

To make matters worse, they ruined all the towels and bedding and left the home in such a filthy condition that it took three cleaners six hours to deep clean, costing us extra. I documented everything with photos and estimates and submitted a reimbursement claim to Airbnb for $581.62. Now, we wait to see whether the guest takes responsibility—or if Airbnb will cover the damages, which I suspect they will.

Lessons From the Chaos

So, that was last week—and it definitely sucked.

Most “gurus” (myself included) will tell you how great short-term rentals are—and they are, most of the time. But a week like this are a reminder that it’s not all passive income and easy profits. You have to be ready for unexpected expenses, maintenance surprises, and situations that test your patience. Most importantly, have a great housekeeping and maintenance team available immediately to resolve any issue.

Challenges come with the territory, but you can weather just about anything this business throws your way provided you have the right people and processes in place.