Cabin Culture

Today's episode is admittedly unsexy—but it's one of those things I wish someone had explained to me in plain language before I needed it. We're talking about 1031 exchanges, which you've probably heard of if you own investment property, but might not fully understand unless you're an accountant or deeply embedded in real estate. This is for the rest of us—the cabin owners who've never sold a property before but are considering it, or anyone who wants to understand their options when it comes to the tax implications of selling an investment property without needing a finance degree to decode it.

I'm sharing our experience from this summer when we sold two properties and purchased one new property, intending to use a 1031 exchange to defer capital gains taxes and simplify our portfolio. The plan was straightforward: sell our cabin in Boone and our long-term rental in Durham, combine those funds, and buy a historic triplex in Boothbay Harbor, Maine—mortgage-free. Except two weeks before closing, I discovered something called "mortgage boot" that completely upended our strategy and forced us to restructure everything. We went from planning to own a property without debt that would generate significant monthly income, to taking on a mortgage we hadn't anticipated and dramatically changing our financial projections. If we had been relying on that rental income for monthly expenses, this would have been a crisis. Thankfully we weren't, but it was still a wake-up call about how much I didn't know.

In this episode, I walk through what a 1031 exchange actually is, the incredibly tight timeline you're working with (45 days to identify properties, 180 days to close), what qualifies as "like-kind property," and most importantly, what boot is and why mortgage boot specifically can derail your entire strategy if you're trying to simplify rather than expand. I also get honest about the privilege that allowed me to invest in real estate in the first place, my complex feelings about capital gains taxes and wealth redistribution, and why real estate investing appealed to me over traditional stock market investments after watching my mom save diligently for a retirement she never got to enjoy. Whether you're actively considering selling a cabin or investment property, curious about tax strategies, or just want to understand these financial tools better, this episode breaks it all down without the jargon—and hopefully saves you from making the same mistakes I almost made.

Instagram: @cozyrockcabin

Cozy Rock Cabin: https://staycozycabin.holidayfuture.com/listings/311027
Cozy Camp Sebec: https://staycozycabin.holidayfuture.com/listings/311051
Cozy Rock Website: http://www.staycozycabin.com

YouTube Channel: https://www.youtube.com/channel/UC_FgMwAgvORd1IwlH1nlC9g

Today we're welcoming Diana Pasquali, who started hosting on Airbnb in the very early days—back when you literally rented an air mattress in your San Francisco apartment. What began as shared-space hosting evolved into Rockridge Casita, a stunning 300-square-foot converted garage that became one of the OG tiny spaces showcasing beautiful design for short-term rentals. Featured in Sunset Magazine in 2017, the backyard ADU made back its entire investment in just one year. But this conversation isn't about building an Airbnb empire. Diana shares why she refuses to expand into urban properties during the Bay Area's housing crisis, and the fascinating story of why she walked away from a nearly-complete $2 million prefab cabin project at Donner Summit after two years of planning—realizing that pandemic construction costs, 20 feet of annual snowfall, and extreme remote management logistics made it unsustainable. Instead, she pivoted to buying an existing 1979 cabin in Truckee that needed renovation but offered actual road access and neighborhood support.

What makes this conversation valuable is Diana's willingness to share the messy middle—knowing when to walk away from sunk costs and choosing the right project over the ambitious one. We talk about renovation budgeting, designing intentionally for guests after a decade of hosting experience, and why she's spending a year hunting vintage Tahoe mugs on eBay instead of rushing to open—because character and personality are what guests remember, not Pinterest-perfect uniformity. Whether you're mid-project and questioning your path or simply want practical design advice from someone who prioritizes community impact alongside financial goals, this offers honest perspective on doing cabin hosting with intention and integrity.

Instagram: @rockridgecasita & @camp.hansel

Booking Site: https://www.rockridgecasita.com

Instagram: @cozyrockcabin

Cozy Rock Cabin: https://staycozycabin.holidayfuture.com/listings/311027
Cozy Camp Sebec: https://staycozycabin.holidayfuture.com/listings/311051
Cozy Rock Website: http://www.staycozycabin.com

YouTube Channel: https://www.youtube.com/channel/UC_FgMwAgvORd1IwlH1nlC9g

Today's episode is a solo deep dive into one of the biggest decisions you'll face on your cabin journey: should you renovate an existing property or build from scratch? This question came up recently when one of my best friends started asking about investing in a second property, and I realized how many of you might be wrestling with this same choice right now. While I love interviewing other folks in the cabin world, I'm finding that these focused solo episodes help those of you looking for specific, targeted answers as you get started on your own cabin and short-term rental hosting journey.

I'm speaking from direct experience here—I've done both. My first primary home was a full gut renovation, a $65,000 mill house in Durham, North Carolina that I brought back to life. Then came Cozy Rock, our ground-up build that's now our highest revenue generator and honestly, my favorite place to be in the world. Most recently, we tackled Cozy Coast in Boothbay Harbor, a 195-year-old property where we're discovering design choices from another era and making decisions that pay respect to the people who lived there before us. Each project taught me something different about the unique advantages and very real challenges of renovation versus new construction.

This isn't about which option is "better"—there's no universal right answer here. Instead, we're going to walk through the practical realities of both paths. We'll talk about cost considerations (and why I'm skeptical of "good deals" in real estate), the character that comes with breathing life back into an old space versus the creative freedom of a blank slate, the infrastructure challenges you'll face with each approach, and why finding the right builder might be the single most important decision you make. I'll also share some hard truths, like how 50 to 75% of people I've talked to who've been part of a build have borderline horror stories, and why digging a well can cost anywhere from $7,000 to $50,000 with no way to predict which end of that spectrum you'll land on. Whether you're drawn to the path of least resistance or ready to chase a dream that doesn't yet exist, this episode will help you think through which approach might be the right fit for where you are in your life right now.

Instagram: @cozyrockcabin

Cozy Rock Cabin: https://staycozycabin.holidayfuture.com/listings/311027
Cozy Camp Sebec: https://staycozycabin.holidayfuture.com/listings/311051
Cozy Rock Website: http://www.staycozycabin.com

YouTube Channel: https://www.youtube.com/channel/UC_FgMwAgvORd1IwlH1nlC9g