Mastering Mid-Term Rentals

In this episode of the Hospitable Hosts podcast, we welcome Bailey Kramer, a real estate investor and entrepreneur who started his real estate journey with short-term rentals and co-hosting and then transitioned to mid-term rentals. Now Bailey owns and manages a portfolio of 10 mid-term rental properties and hosts a podcast, The Mid-Term Rental Show, for active and aspiring mid-term rental operators.   

In the episode, Bailey shares his real estate journey, why he switched to mid-term rentals, and how he uses technology to simplify routine property management tasks. He also discusses the biggest misconceptions about mid-term rentals and the opportunities to run mid-term rentals as short-term rentals during peak seasons.

Press Play now to discover growth opportunities that mid-term rentals offer for vacation rental hosts and property managers, and how embracing automation tools like Hospitable can help you succeed.

Do you prefer to read the highlights? We’ve got a summary of the key takeaways below.

Switching to Mid-Term Rentals

Bailey started his real estate journey with short-term rentals and co-hosting about four to five years ago. “I was initially running 30 short-term rentals back in my peak of the co-hosting days, and there's no doubt that I could not have done that without Hospitable,” Baily says.

Now, Bailey focuses on owning his own properties. He explains that he transitioned to mid-term rentals because, even with systems, software tools, and employees, running 30 STR properties across different cities was not easy for him.

“Once I had the experience of running all those properties, I also built up enough cash myself to where I was able to be on the owning side of the business. So that was always the long-term goal for me to own the properties, but co-hosting was definitely a nice gateway to get there,” Bailey explains.

The Biggest Misconception about Mid-Term Rentals

Bailey notes that many people don’t think that mid-term rentals are as profitable as short-term rentals. In fact, the profitability of rental properties depends on multiple factors. Short-term rentals, on average, may earn more revenue, especially during high season. Still, they come with constant turnover and guest expectations for the property to be perfect from top to bottom.

“Of course, you're going to likely earn more money than if you're doing just a mid-term rental, but, again, it's that constant turnover that has a bunch of hidden costs in it. Or if you've been running short-term rentals for a while, you know, they're not too hidden, and you need to factor in all of these expenses.”

Using Hospitable

Bailey underlines that although his portfolio and strategy have changed, he is still using Hospitable to automate routine tasks and manage his properties more efficiently.

“One feature that I absolutely love is the integration with the Schlage smart locks. Whether they're staying for three nights or three months, that stays the same, like having the automated door codes.”

Bailey admits that with mid-term rentals, he is doing a lot more tasks manually, such as adding bookings manually in Hospitable for “insurance guests” who need a place to stay for three to six months.

“I'm still manually doing it through Hospitable, but it takes one minute to add them in, and that automatically generates the door codes, the check-in messages, and notifies my cleaning team. So the functionality hasn't really changed for me.”