[REAL STORIES] Rent-Stabilized in the West Village. Vacation homeowner in Connecticut. episode artwork

EPISODE · Mar 3, 2026 · 40 MIN

[REAL STORIES] Rent-Stabilized in the West Village. Vacation homeowner in Connecticut.

from Second Home First · host Second Home First

If you’re a self-employed freelancer and think getting a mortgage, especially on a second home, just isn’t possible, this week’s episode is for you. Our guest, a New York City–based travel journalist, didn’t want to give up his rent-stabilized apartment in the West Village. So instead of stretching to buy in Brooklyn, he leveraged little-known lending options to purchase a mid-century modern fixer-upper in Connecticut— turning his love of architecture from something he writes about into something he actually owns. This Week’s Guest: Paul Jebara is a freelance journalist who writes about travel, architecture and design. Even though he has found the unicorn of Manhattan real estate—a rent-stabilized apartment in the coveted West Village—he considered giving it up to buy in Brookly. But as his search went on, his budget kept climbing, the neighborhoods he could afford kept getting further out, and the compromises within the space kept stacking up. Eventually, Paul decided to keep renting in the West Village and buy his second home first, a mid-century modern fixer upper in Litchfield County, Connecticut. Tune in to learn: -Why buying a fixer-upper became Paul’s strategic advantage to avoid bidding wars -How writing a thoughtful letter to the sellers helped Paul’s lower-priced offer win out -How Paul navigated financing as a longtime freelancer, including mortgage options available to self-employed buyers that many traditional lenders don’t even know about ***Paul is currently a “Sweet Spotter”. Take the quiz to determine what type of Vacation Home Owner you would be: BuyYourSecondHomeFirst.com/quiz Want to buy a vacation home that pays for itself? Learn more about the Second Home First Academy at BuyYourSecondHomeFirst.com/Academy Key links: –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] A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Minoan: https://www.Minoan.com/SecondHome Use the link provided to sign up and receive a free $25 in credit. 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

If you’re a self-employed freelancer and think getting a mortgage, especially on a second home, just isn’t possible, this week’s episode is for you. Our guest, a New York City–based travel journalist, didn’t want to give up his rent-stabilized apartment in the West Village. So instead of stretching to buy in Brooklyn, he leveraged little-known lending options to purchase a mid-century modern fixer-upper in Connecticut— turning his love of architecture from something he writes about into something he actually owns. This Week’s Guest: Paul Jebara is a freelance journalist who writes about travel, architecture and design. Even though he has found the unicorn of Manhattan real estate—a rent-stabilized apartment in the coveted West Village—he considered giving it up to buy in Brookly. But as his search went on, his budget kept climbing, the neighborhoods he could afford kept getting further out, and the compromises within the space kept stacking up. Eventually, Paul decided to keep renting in the West Village and buy his second home first, a mid-century modern fixer upper in Litchfield County, Connecticut. Tune in to learn: -Why buying a fixer-upper became Paul’s strategic advantage to avoid bidding wars -How writing a thoughtful letter to the sellers helped Paul’s lower-priced offer win out -How Paul navigated financing as a longtime freelancer, including mortgage options available to self-employed buyers that many traditional lenders don’t even know about ***Paul is currently a “Sweet Spotter”. Take the quiz to determine what type of Vacation Home Owner you would be: BuyYourSecondHomeFirst.com/quiz Want to buy a vacation home that pays for itself? Learn more about the Second Home First Academy at BuyYourSecondHomeFirst.com/Academy Key links: –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] A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Minoan: https://www.Minoan.com/SecondHome Use the link provided to sign up and receive a free $25 in credit. 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

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[REAL STORIES] Rent-Stabilized in the West Village. Vacation homeowner in Connecticut.

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This episode is 40 minutes long.

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This episode was published on March 3, 2026.

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If you’re a self-employed freelancer and think getting a mortgage, especially on a second home, just isn’t possible, this week’s episode is for you. Our guest, a New York City–based travel journalist, didn’t want to give up his rent-stabilized...

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