From Military Housing to Boutique Hospitality: How Blake Dailey Built a $25 Million Resort Portfolio

Written by:

Steve Marcinuk

Date:

22 Jan 2026

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The boutique hotel industry is undergoing rapid change as more travelers seek distinctive, experience-driven stays instead of standardized accommodations. Blake Dailey, CEO and founder of Stayvest, has built an eight-property, $25 million portfolio by focusing on the often-overlooked middle tier of hospitality real estate – properties too large for individual investors but too small for institutional players.

Dailey’s entry into real estate began during his time as a newly commissioned Air Force lieutenant. He and his wife, Nicole, started with less than $2,200 in their bank account and a negative net worth, and bought a house with a mother-in-law suite, converting part of it into an Airbnb rental. The rental income covered their living expenses and even produced a small monthly profit. “It was the positive reinforcement needed—this real estate thing is pretty cool,” Dailey recalls.

Targeting the Overlooked Middle Market

Dailey’s strategy focuses on acquiring properties in the $2 million to $5 million range—a segment often overlooked by individual investors, who see the price point as too high, and by large institutional buyers, who consider it as too small to scale. “There’s this really nice sweet spot for acquisitions between two to five million because it’s too big for the small everyday investor, but too small for your big brands, private equity, or hedge funds,” Dailey explains.

By targeting these properties, Stayvest can find hotels with significant potential for value improvement. Dailey points to recent projects in Blue Ridge, Georgia, where Stayvest acquired properties for about $3 million each and invested in upgrades and new amenities. He expects some of these properties to approach or exceed $10 million in value after renovations.

Stayvest operates as a vertically integrated company, handling acquisition, renovation, operations, and marketing internally. With about 25 employees and $5 million in annual revenue, the company competes effectively against much larger hospitality firms by focusing on execution and operational efficiency.

The Rise of Experiential Travel

Shifting guest preferences are fueling demand for boutique hotels that offer unique experiences. Dailey notes that 81% of travelers now begin their trip planning on social media, especially among Gen Z and millennials. This has changed how hotels must market themselves and what guests expect from their stays.

“You’re really selling experience. You’re not really selling a room,” Dailey says. Traditional mid-level hotel chains like Hampton Inn or Holiday Inn offer consistency but lack the local character and amenities modern travelers want. In contrast, unique boutique properties can command much higher rates. “You see up to a 60% premium in your revenue per available room with boutiques. In the same market, you could have $169 versus $100 a night in the boutique space,” Dailey explains.

This premium comes from travelers’ willingness to pay more for properties that reflect the local area and offer features they can’t find elsewhere. At Stayvest’s Blue Ridge locations, guests have access to A-frame cabins with private hot tubs and lake platforms with fire pits—amenities that directly support higher nightly rates and occupancy.

Market Selection and Seller Financing

Understanding the target guest is key to Stayvest’s market selection process. Dailey emphasizes that travel motivations vary by region and season, requiring tailored strategies for each location. “You have to understand who your avatar is who’s coming there. That’s going to be different in Miami versus Seattle versus Oklahoma City versus New York City. People go there at different times of the year for different reasons.”

Financing plays a central role in Stayvest’s growth. Six of the company’s eight acquisitions have used seller financing, which allows for faster closings and avoids bank underwriting hurdles. Dailey targets sellers who have owned properties for many years, accumulated substantial equity, and are ready to move on but lack the resources or energy to renovate and reposition their hotels. “A lot of times, it’s those owners that have higher equity; they’ve owned the hotel for a long time, but they’ve phased out. Every year it gets a little worse, deferred maintenance piles up,” he explains.

By offering a higher sale price through seller financing, Stayvest can close quickly while meeting sellers’ financial goals. This approach has allowed the company to acquire and reposition underperforming properties that institutional investors overlook.

Building a Community of Military Investors

More than half of Stayvest’s investors are current or former members of the military. Dailey has focused on educating this group about using self-directed IRAs and retirement funds to invest in private real estate deals. “I just think that’s so cool, being able to provide those opportunities that your typical captain or staff sergeant or major in the Air Force or Army is not going to have access to,” he says.

Stayvest’s investor club also offers lifestyle perks, including free nights at the company’s properties. This helps investors connect with their investments tangibly, instead of simply owning a share in a distant commercial asset. “You can actually come share with your family what you’re investing in,” Dailey says.

Overcoming Scaling and Exit Challenges

The middle-market focus that gives Stayvest its acquisition edge also poses challenges when it comes to selling. I learned this daily when trying to sell two Panama City Beach properties individually. Each property, generating $500,000 to $600,000 in annual revenue, was too large for individual owner-operators but too small for regional buyers. “We didn’t have buyers on either one. Nobody could pay 1.5 to 2 million for each deal,” Dailey recalls.

By bundling the properties into a single package, Stayvest attracted a regional hotel buyer. “As soon as we combined them—more revenue, more scalable operation, you could support a team—then we had a regional hotel buyer out of Florida ultimately be our end buyer,” he explains. This experience showed the importance of reaching at least $1 million in annual revenue to appeal to larger, more sophisticated buyers. Properties with annual revenue below $700,000 often lack the margins to support professional management, limiting the buyer pool.

The Future of Boutique Hospitality

Looking forward, Dailey expects major hotel brands to continue acquiring or developing boutique properties. Marriott, Hilton, and Wyndham have all launched or expanded boutique divisions to capture the growing demand for experiential stays. However, Dailey believes the real competitive advantage lies in owning the customer relationship and building a direct brand presence, primarily through social media.

“If you can create that following around your property, create the brand with your property, and you control your customer acquisition, that cuts off a lot of uncertainty that bigger buyers have,” he says. By understanding the cost of acquiring each guest and maintaining a strong online presence, boutique operators can reduce business risk and attract strategic buyers.

For real estate investors, Dailey’s path shows that there are substantial opportunities in the hospitality sector’s overlooked middle ground. By targeting properties that small investors find too complex and large funds find too small, and by delivering authentic, locally rooted guest experiences, companies like Stayvest are well-positioned to benefit from ongoing shifts in how people travel.

As travelers continue to prioritize unique, memorable stays over traditional hotel brands, operators who can deliver on these expectations – and who understand both the operational and financial nuances of the middle market – are likely to see both strong guest demand and attractive investor returns in the years ahead.