Making Luxury Livable— And Profitable Jonathan Steingraber knows real estate. As an entrepreneur, coach, speaker, and investor— he has spent his career helping others turn property into opportunity. Whether leading workshops through Investors Rock Academy or scaling one of New Jersey’ s fastest-growing brokerages with his wife, Michelle Pais, Jonathan’ s philosophy is simple: your assets should work as hard as you do.
Through years of coaching and investing, one question comes up time and again: What’ s the smartest way to approach a vacation home? Below, Jonathan unpacks three clear strategies, each backed by real numbers and real stories. Should you buy and keep it for your family? Rent it out when you’ re not using it? Or skip ownership entirely and just rent when the mood strikes? The answer depends on what you’ re really looking to gain— from returns to rituals.
The Modern Vacation Home Dilemma It begins with a fantasy. A sea breeze. A chilled glass of Sancerre. The kind of stillness that makes your inbox irrelevant. But as alluring as the idea is, the real question lingers: Should you own that dream, rent it for a season, or let others pay for it while you sneak in a few golden weekends of your own?
Welcome to the modern dilemma of the affluent New Jerseyan.
In the era of bespoke everything— from cocktails to concierge banking— your vacation strategy deserves equal attention. Let’ s examine the options, the data, and the real-world stories behind the homes that shape our best memories.
1. Buy It And Keep It All To Yourself This is the legacy play. It’ s full control, full privacy, full immersion— and full responsibility. No renters, no turnover headaches, and no strangers touching your espresso machine.
Financial Snapshot( Example: $ 2M NJ Shore Home)
• Purchase Price: $ 2,000,000
• Property Taxes & Insurance: $ 3,000 / month
• Maintenance / Repairs / Utilities: ~$ 2,000 / month
• Annual Outlay: ~$ 60,000 / year
Pros
• Spontaneous escapes year-round
• Long-term appreciation potential
• Personalization without compromise
• Legacy asset for future generations
Cons
• High carrying costs whether used or not
• Time and effort for upkeep
• Tied-up capital
21