Five Resolutions to Make 2026 the Year You Buy a Vacation Home (That Pays for Itself!)

Owning a vacation home that pays for itself sounds like a dream—but what happens when managing that property starts to feel like a second job? Today’s expert guest is pulling back the curtain on management companies, sharing what you really get for your money, the red flags to look out for, and how to decide when it might be time to hand over the reins. This Week’s Expert Guest: Jason Muth is the co-founder of Prideaway Stays, a boutique vacation rental management company based in Provincetown, Massachusetts, and the host of the SmartStay podcast. Jason shares what it's really like to work with a property management company, including what services they provide, how much they charge, and how to decide whether hiring one makes financial sense. Tune in to Learn: –When to hire a property manager versus self-manage your vacation rental –What management companies charge and how their fees affect your profits.The key green flags and red flags to look out for when choosing a property manager –How to handle guest feedback and decide which complaints are worth addressing –How to calculate the opportunity cost of enjoying your vacation home versus renting it out Key links: –Second Home First Academy: BuyYourSecondHomeFirst.com/academy *Use code PODCAST for 40% off –Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe –Visit the website: BuyYourSecondHomeFirst.com –Follow on Instagram and TikTok: @BuyYourSecondHomeFirst –Find us on Substack: SecondHomeFirst.Substack.com –Say Hi! [email protected] (mailto:[email protected]) A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Click the link and enter code HOME20 for an additional 20% off their yearly and bi-yearly plans. Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services. Turno: https://go.turno.com/second_home_first Use the link provided to get $25 off your first clean. Flytographer: https://www.Flytographer.com/SHF Use code SHF25 for $25 off your first shoot PriceLabs: https://hello.pricelabs.co/signup/?referral=secondhomefirst Use code SecondHomeFirst (all one word) for a 30-day free trial, plus $10 off your first invoice

When most people think of an impulse buy, they probably think of a new pair of shoes. But for today’s guest, it was a beach crash pad. After feeling like he missed his chance to buy in New York City due to climbing real estate prices post-Covid, this banker decided to keep renting in Williamsburg and buy his “second home” first on Long Island in Long Beach. This Week’s Guest: Michael “Phase” Phelan has built an insanely successful career in banking and had considered buying a primary home in Williamsburg, where he’s been renting for more than a decade. But then, he made what he calls an “impulsive” decision and decided to buy his second home first: a one-bedroom condo in Long Beach. He plans to use the home as a beach crash pad for now and, eventually, turn it into a long-term rental. Tune in to Learn: –Why Phase chose to buy a vacation home in Long Beach instead of a primary home in Brooklyn –How he found a beachside condo for a fraction of the price of buying in NYC –Why buying a second home first can take the emotion out of real estate decisions –The biggest lessons from navigating the home-buying process as a first-time buyer –How Phase plans to enjoy his beach getaway now and turn it into a long-term rental in the future Key links: –Second Home First Academy: BuyYourSecondHomeFirst.com/academy *Use code PODCAST for 40% off –Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe –Visit the website: BuyYourSecondHomeFirst.com –Follow on Instagram and TikTok: @BuyYourSecondHomeFirst –Find us on Substack: SecondHomeFirst.Substack.com –Say Hi! [email protected] (mailto:[email protected]) A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Click the link and enter code HOME20 for an additional 20% off their yearly and bi-yearly plans. Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services. Turno: https://go.turno.com/second_home_first Use the link provided to get $25 off your first clean. Flytographer: https://www.Flytographer.com/SHF Use code SHF25 for $25 off your first shoot PriceLabs: https://hello.pricelabs.co/signup/?referral=secondhomefirst Use code SecondHomeFirst (all one word) for a 30-day free trial, plus $10 off your first invoice

Second Home First is going international! This episode kicks off our brand-new Second Home First Abroad series with a trip to Italy, where a Chicago lawyer is transforming an old farmhouse into two luxury suites, complete with a pool, a sauna in the former stables, and a wine tasting room in the old cantina. This Week’s Guest: Claire Stephens is a lawyer who lives in Chicago but decided to buy a property in Liguria, Italy. This isn’t just any property, but a farmhouse next door to a home that’s been in her family for generations. She talks about challenges of buying a property in a different country from where you live—not to mention, in a different language! And she reminds us that while this is a slow process, something she estimates will take about five years, the finished product isn’t the only part of the process she’s looking forward to. Tune in to Learn: —What it’s really like to buy a home in Italy as a foreigner —The importance of building relationships with the local community —How to find and build a trusted local team you can rely on —Claire’s renovation plans for the property and the timeline —Why building strong relationships can be your biggest advantage when investing overseas. Key links: –Second Home First Academy: BuyYourSecondHomeFirst.com/academy *Use code PODCAST for 40% off –Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe –Visit the website: BuyYourSecondHomeFirst.com –Follow on Instagram and TikTok: @BuyYourSecondHomeFirst –Find us on Substack: SecondHomeFirst.Substack.com –Say Hi! [email protected] (mailto:[email protected]) A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Click the link and enter code HOME20 for an additional 20% off their yearly and bi-yearly plans. Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services. Turno: https://go.turno.com/second_home_first Use the link provided to get $25 off your first clean. Flytographer: https://www.Flytographer.com/SHF Use code SHF25 for $25 off your first shoot PriceLabs: https://hello.pricelabs.co/signup/?referral=secondhomefirst Use code SecondHomeFirst (all one word) for a 30-day free trial, plus $10 off your first invoice

The housing market is constantly making headlines, whether it’s rising home prices, high interest rates, or a shortage of homes for sale. But today, we’re hearing from someone who covers the topic for one of the most influential publications in the world: the New York Times. Real estate journalist, Heather Senison, who wrote the full-page feature on Second Home First, is here to share what she’s seeing from today’s homebuyers—and where homeownership could be headed next.

After her husband was involved in a serious car accident while on his way to a work conference, today’s expert guest began to reevaluate everything. What followed was a leap of faith to create more time and freedom for her and her family, while also solving a problem for others that they had experienced firsthand.