Case Study: John Palumbo“ I saw it as a long-term investment— something to pass down. The best part? Quality time. The worst? Maintenance. If you’ re going to do it, choose a location that’ s close enough to make spontaneous weekends possible. And trust me: get a pool.”
Smart Money Insight Owning a second home isn’ t about the numbers working— it’ s about what it does for your family. That, Jonathan insists, is priceless.
2. Buy It And Rent It( Strategically) This option blends lifestyle with ledger. You use the house when it matters most, and when you don’ t, it pays for itself— or better.
Rental Income Potential( Based On AirDNA / MLS Data)
• High Season( June – Aug): $ 700 –$ 1,000 / night = ~$ 50,000
• Off Season: $ 15,000 –$ 20,000
• Net Income After Costs: ~$ 60,000
Pros
• Offsets carrying costs
• Keeps property in great shape
• Flexibility to choose your dates
Cons
• Increasing regulations on short-term rentals
• Wear-and-tear from guests
• Becomes a hospitality business
Case Study: Jacquelyn Villano“ I wanted to invest but wasn’ t ready for a fulltime tenant. We use the house year-round, and the rentals cover the expenses and then some. My advice? Research local ordinances— Airbnb isn’ t welcome everywhere. And hire a killer cleaning team. You can’ t host without it.”
Smart Money Insight Owning a second home and never renting it is like buying a yacht and leaving it at the dock for the Instagram photo.
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