Short Term Rental Problems and Solutions

Most short-term rental deals don’t fall apart at purchase. They fall apart in operations.

In this episode, I sit down with Steven, a Pocono investor who did everything right. He spent two years searching for the right property, invested over $100,000 into improvements, and hired professional management expecting a hands-off experience. Instead, he got poor performance, bad communication, and numbers that didn’t add up.

Now he’s facing a decision a lot of owners quietly consider, fix the operation himself, or sell and move on.

I manage over 130 short-term rentals in the...

Jeremiah opens this episode with a reality check every aspiring Airbnb host eventually learns the hard way: buying the property is the easy part. The real challenge is understanding the operational costs, guest expectations, management headaches, and financial realities that come after the closing table.

In this episode of Short Term Rental Problems and Solutions, Jeremiah sits down with Scott, a future short-term rental owner planning a new build in the Poconos. Together, they break down what it actually takes to build and operate a profitable Airbnb in today’s market, from underwriting the deal and estimating ex...

Everyone thinks building a short-term rental is a shortcut to passive income, until they realize they’re coordinating site work, navigating HOA rules, and trying to predict returns on something they’ve never done before.

If you’re serious about getting into the short-term rental space, this is the conversation you need to hear.

In this episode of Short-Term Rental Problems and Solutions, I sit down with Scott, who’s actively looking to build a modular cabin in the Poconos. We break down the real decisions investors face before they ever book their first guest, includin...

Everyone thinks building a short-term rental is a shortcut to passive income, until they realize they’re coordinating site work, navigating HOA rules, and trying to predict returns on something they’ve never done before.

If you’re serious about getting into the short-term rental space, this is the conversation you need to hear.

In this episode of Short-Term Rental Problems and Solutions, I sit down with Scott, who’s actively looking to build a modular cabin in the Poconos. We break down the real decisions investors face before they ever book their first guest, includin...

I hope you’re lucky, because expecting Airbnb to back you up and follow their own policies can feel like a roll of the dice, you'll have better luck at a casino.

If you’ve ever had a guest rave about your property and still leave you four stars, you already know something isn’t adding up.

In this episode of Short Term Rental Problems and Solutions, we break down one of the most frustrating parts of running a short-term rental, the review system. Not the version you think exists, but the one you actually have t...

Starting a property management company can be an incredible opportunity… if you’re wired for it.

There’s real upside here, scaling systems, building a team, growing beyond a single property, and creating something that has real value. But it’s not the same as managing your own short-term rental, and the gap between those two is where most people either level up… or burn out.

In this episode of Short Term Rental Problems and Solutions, we break down what actually happens when you go from managing your own Airbnb or vacation rental to managing other peop...

When I moved here I didn't know the risk I was taking buying a home with a septic system. Chances are most investors don't know either. They are one of the most expensive repairs possible at a rural property and they are absolutely necessary. Its hard to understate just how bad it is going into rental properties in the mountains without being educated or at least guided by these realities.

In this episode I answer a listener's question about the suspicious connection between three plumbing repairs in just 6 weeks. He's being told to sue the seller, but...

This episode dives into the essential process of finding a top-tier property manager who aligns with your goals. Because choosing wisely can be the difference between a $60k year and a $120k year. We’ll break down where most people search, Google, ChatGPT, or just referrals, and why you should take it further. We’ll reveal what questions to ask from tech to cleaning fees to their accountability so you find a partner, not just a vendor. Plus, we’ll share expert strategies (like using AirDNA) to uncover high-performing PMs and ensure they’re invested in your success long-term. Let’s el...

In this episode of Short Term Rental Problems and Solutions (formerly STR Problems, Strong Solutions), we tackle a question that hits most short-term rental owners eventually, not just about profit, but about time. When does managing a short-term rental stop being worth the effort, and when does converting to a long-term rental actually make more sense?

We break down the hidden time demands behind short-term rentals, guest communication, cleaning coordination, maintenance calls, pricing adjustments, and the constant need to stay “on-call.” Then we compare that to long-term rentals, where the workload shifts from daily involvement to periodic issu...

In this episode, we talk all about burnout in the world of property management and short-term rentals. I explain practical steps you can take, like giving your hardworking team a chance to enjoy the property themselves, and finding ways to expand thoughtfully, so that you can keep delivering great guest experiences while avoiding exhaustion. When your team stays refreshed, your reviews shine, and you stay in control. Burnout can happen, but with these strategies, your success and well-being are both possible.

This episode was recorded live at the conference, so the visual aid is more available on...

Guest damage doesn’t just affect one stay, it can quietly impact the experience of every guest who comes after. It also can create unbelievable risk depending on what it is the cleaners are not reporting.

In this episode of STR Problems, Strong Solutions, Jeremiah breaks down how unnoticed damage leads to safety risks, bad reviews, and long-term reputation problems for short-term rental hosts. The conversation also explores the reality of managing cleaning teams, the different types of cleaners operating in vacation rental markets, and the accountability systems needed to maintain consistent standards.

Je...

Here we welcome Jenny Snow to answer a listener's question about airbnb increasing their host fee by 5 times! Jenny is the Poconos Airbnb Community Leader so shes faced with these types of questions constantly. We go through what hosts need to do to adapt to this change and then move onto understanding the algorithm and how to get on page one of search results reliably. Coming from Jenny this conversation is a fun one that you will want to take notes for.

Also discussed is linen rentals, security cameras, and how hosts increase their revenue by keeping...

Here we welcome Jenny Snow to answer a listener's question about airbnb increasing their host fee by 5 times! Jenny is the Poconos Airbnb Community Leader so shes faced with these types of questions constantly. We go through what hosts need to do to adapt to this change and then move onto understanding the algorithm and how to get on page one of search results reliably. Coming from Jenny this conversation is a fun one that you will want to take notes for.

Also discussed is linen rentals, security cameras, and how hosts increase their revenue by keeping...

In this episode, we unravel the mystery behind a jaw-dropping $1,000 electric bill. First, we walk you step-by-step through an energy audit for your rental, highlighting surprising energy drains and unexpected savings. We then dig into heating systems based on reliability, redundancy, and some cautionary tales of cost-cutting gone wrong, including my own facepalm moment. Finally, we explore smart thermostat strategies. Thats how to stay in control without leaving your guests out in the cold. It’s a warm, energy-savvy journey you won’t want to miss!

Bears aren’t a guest complaint you can solve with better communication, and if you manage a short-term rental in a rural or mountain market, unsecured trash can turn into a neighbor problem fast.

In this episode of STR Problems, Strong Solutions, Jeremiah answers a listener question from a self-managing Airbnb owner dealing with bears knocking over trash, frustrated neighbors, and the reality of being two hours away when it happens. We break down what vacationers reasonably expect, and how rural trash collection differs from suburban norms.

You’ll learn what actually works to keep bear...

This is for two types of people. Those who have a good cleaner and don't want anything to change, and those who recognize their cleaner can do a better job. Tune in for some tips on how to approach that conversation in a way that will build the relationship instead of hurting it.

The podcast episode addresses Ravi's dilemma with his cleaner and provides insights into maintaining a rental property. It emphasizes the importance of confrontation in relationships and the constant energy required to maintain a property.

Takeaways

The decision to allow pets in a rental can be a tough one. Its hard to predict the impact at the beginning. And our guest question today dives into the dynamic between Mark the owner and his STR property manager. We go through some considerations of ways to make both parties happy where pets are allowed and Mark's allergies are unaffected. Then we discuss the oversupply and under demand of pet free rentals, and we dive into the dynamic of emotional support animals and what you cannot do about it. If you've wondered how you can succeed in rentals...

Lets talk about Hot Tubs. Follow along as we get into a puzzle of a hot tub that was found empty, but without any leaks. We also discuss good hot tub rules, liability, freezing temperatures, water quality, and other off topic stuff that Jeremiah thinks about randomly.

Takeaways