Short Term Rental Problems and Solutions

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Listing Optimization: Can This Airbnb be Saved?

2026-10-0843:55

He spent $80,000 furnishing and improving his Airbnb. Now he’s considering selling because the property isn’t performing the way he expected.So in this episode, I pull up his listing and go through it live, photo by photo, room by room, with no sugarcoating.The problem isn’t necessarily that he didn’t spend enough money. It’s where the money went, what the property is trying to be, and how poorly some of its best features are being presented.We get into professional photography, the first five photos, furniture choices, game rooms, hot tubs, fire pits, outdoor lighting, listing descriptions, guest capacity, pricing, pet policies, and one of my biggest concerns: buying the wrong style of house for a vacation rental in the first place.There’s also a bigger lesson here for Airbnb investors. Spending more money does not automatically create more value. A property can have four bedrooms, a hot tub, a game room, two kitchens, and tens of thousands of dollars in furniture and still feel completely average to the guest scrolling through listings.Sometimes the answer is better marketing. Sometimes it’s better design. Sometimes the property needs a different strategy entirely.And sometimes you bought the wrong house.If you own or manage a short-term rental that isn’t performing the way you expected, this episode will give you a long list of things to look at before you simply lower the price.

Guest Red Flags

2026-10-0143:36

What are the biggest red flags when screening Airbnb guests?After thousands of reservations, there are certain things I’ve learned to watch for. A guest books for one person. They ask how many cars fit in the driveway. They want to know how close the neighbors are. They keep changing the guest list. They live nearby. They mention they're an Airbnb host. Or maybe they have 86 reviews.I call these red flags throughout this episode, but if I’m being precise, most of them are really yellow flags.One of these things by itself usually isn't a reason to decline a reservation. But when two, three, or four start showing up together, they can paint a very different picture.In this episode, I answer a listener's question about guest screening and go through the warning signs I've learned to watch for as an Airbnb host and short-term rental property manager.We talk about third-party bookings, local guests, influencers and content creators, unusually high numbers of reviews, slow communication, occupancy questions, long stays that suddenly get extended, moving trucks, fireworks, early arrivals, guest registration issues, and plenty more.Some are obvious. Some sound completely harmless. And a few are probably the exact opposite of what most Airbnb hosts expect.The point isn't to become suspicious of every guest. It's to recognize patterns, ask better questions, and know when a handful of yellow flags are starting to look like one big red flag.If you own or manage an Airbnb, VRBO, vacation rental, or other short-term rental, this episode will give you a better framework for spotting higher-risk reservations before they become expensive problems.

Where to Search for Your STR in 2026

2026-09-2451:28

Where should you buy a short-term rental in the Poconos?Lake Harmony? Albrightsville? Long Pond? Tobyhanna? Pocono Lake?A listener planning his first Poconos STR realized pretty quickly that choosing the right area is more complicated than finding a house close to a ski resort. Township regulations, HOA rules, occupancy limits, registration fees, local politics, property values, and even the size of the surrounding STR market can completely change the risk and potential of an investment.In this episode, Jeremiah breaks down the five townships he focuses on when searching for short-term rental properties in the "Western Poconos:" Kidder, Penn Forest, Tunkhannock, Tobyhanna, and Coolbaugh.We get into Lake Harmony, Towamensing Trails, Indian Mountain Lakes, Brier Crest Woods, Emerald Lakes, Arrowhead Lake, Locust Lake Village, Pocono Country Place, Pocono Farms, Camelback and several other communities along the way.Jeremiah also explains his “dartboard” analogy for understanding Poconos STR demand, why a larger house in the right market can sometimes be more interesting than a property in the center of a tourist destination, and why he believes investors should focus less on finding the “best town” and more on finding a property with strong marketability, value, and manageable risk.Finally, we cover some of the biggest red flags Jeremiah watches for before buying an STR, including restrictive HOAs, areas where vacation rentals are rare, communities dominated by primary residences, and places where regulations have already been challenged or tightened.If you’re considering buying an Airbnb or vacation rental in the Poconos, this episode will give you a much better framework for deciding where to start your search, and what to investigate before you go under contract.

How to Actually Get a Call Back From a Contractor

2026-09-1731:10

Finding a good contractor, property manager, cleaner, or other service provider can be frustrating. You call. You email. You explain exactly what you need.And nobody gets back to you.In this episode, I break down a real email I received from a prospective STR investor who wanted an enormous amount of research before he had even visited the Poconos, let alone purchased a property.The questions weren’t necessarily bad. The approach was.That opens up a much bigger conversation about how to actually find good service providers and get them interested in working with you.I’ll explain how I would approach a busy contractor or property manager, what I would ask on the first call, how to get useful information without asking someone to do hours of unpaid homework, and why doing some of the research yourself can completely change the conversation.We also get into rental projections, comparable STR performance, owner use, why rental history can sometimes be misleading, and a real Village at Camelback example that shows how management strategy can dramatically change a property's numbers.If you own or are considering buying a short-term rental, this episode is about more than getting someone to call you back. It’s about learning how to identify good service providers, respect their time, ask better questions, and become the kind of client the best people actually want to work with.

Septic Systems and Crawlspaces

2026-09-1142:16

Buying a short-term rental can look like a great deal right up until you discover the $40,000 problem hiding underneath it.In this episode of Short Term Rental Problems and Solutions, Jeremiah answers three real questions from STR buyers dealing with expensive issues that are especially common when purchasing rental properties in rural markets like the Poconos.What does it actually mean when a septic drain field is “saturated”? Can you assume the vacant lot next door will work for a replacement septic system? Is an $8,000 mold remediation or $18,000 crawl-space encapsulation really necessary? And what happens when the five-bedroom Airbnb you bought turns out to legally be a three-bedroom property?Jeremiah breaks down how septic systems and hydraulic load tests work, what a failed drain field could really cost, how he approaches moisture and mold in crawl spaces, and why buyers need to understand zoning, septic records, legal bedroom counts, and STR occupancy limits before closing.He also shares a real Poconos example of a rental that grossed $134,000 when marketed for 10 guests, then dropped to $82,000 after local STR regulations limited the property to six guests based on its legal three-bedroom septic system.The lesson throughout the episode is simple: “buyer beware” doesn’t mean you shouldn’t take risks. It means you need to understand the risk before you buy.If you're buying an Airbnb, vacation rental, or investment property in the Poconos or another rural market, this episode covers some of the due diligence that can save you tens of thousands of dollars after closing.Short Term Rental Problems and Solutions is about what STR ownership actually looks like from the inside: the problems, mistakes, operational messes, and strategies that help investors keep learning and keep building.

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Short Term Rental Problems and Solutions