From Military Service to Multi-Property Investors: Daniel & Rachel’s Portfolio Growth Story

Published: October 31, 2025

From Military Service to Multi-Property Investors: Daniel & Rachel’s Portfolio Growth Story

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Many dream of achieving financial independence through real estate, but few execute with the precision and speed of Daniel and his wife Rachel. A retired Air Force veteran with a full-time job, Daniel and his wife have built an impressive portfolio of 16 properties and 26 doors in just five years. His journey from hesitant aspiring investor to seasoned real estate pro offers valuable insights for anyone looking to make their mark in the world of property investment.

The Unexpected Catalyst: Overcoming Landlord Fears

For years, Daniel was hesitant about real estate, often discouraged by the typical “landlord horror stories.” But his wife saw the potential early on and never stopped championing the idea. Her vision and persistence kept it alive. In 2020, after Daniel’s grandfather passed away, she suggested turning his lake house into a rental. Though that plan didn’t materialize, it planted the seed. The idea had taken root—and it was entirely thanks to her. She gets full credit for us pivoting their focus to Florida, where they went on to purchase their first rental property.

The First Step: Dipping a Toe into the Market

With recommendations from a trusted property management company, Daniel and his wife connected with a realtor and purchased their first property in Florida in 2020. This initial investment, a slightly distressed property needing less than $10,000 in repairs, served as their entry point into the market.

“It was just buying a rental property, you know, just kind of like dipping your toes into it,” Daniel explains. The property, bought for around $130,000, was intended solely for rental income, with a long-term vision of potentially using it later, though not as their immediate future home.

A Fortuitous Sale and Explosive Growth

The first property proved to be an unexpected success. After two years with the same tenant, Daniel visited the property and had a casual conversation with her. To his surprise, she expressed interest in buying the house. During the COVID-19 pandemic, property values had soared, and the house had appreciated significantly, jumping to approximately $200,000.

Daniel and his wife seized the opportunity, selling the property privately to the tenant. This single transaction yielded a $70,000 profit, which became the fuel for their rapid expansion. They used the proceeds to purchase three more properties, kickstarting their impressive portfolio growth.

Strategic Expansion: From Single-Family to Multi-Family and Beyond

The initial success propelled Daniel and his wife to think bigger. They purchased another townhouse in their preferred military town in Florida, leveraging the high demand from young military members for easy-to-rent properties. Then, they decided to diversify geographically, acquiring two triplexes in Pennsylvania. This move significantly boosted their “door count,” adding six income-producing units at once.

Today, Daniel’s portfolio boasts 16 properties and 26 doors, including a mix of fourplexes, triplexes, duplexes, townhouses, and single-family homes, with all but one currently rented.

Financing the Dream: Leveraging Smart Capital

Daniel’s early investments were self-funded. He and his wife strategically leveraged saved money, 401(k) loans, and most significantly, a Home Equity Line of Credit (HELOC) on their primary residence.

Once they had accumulated about six or seven properties, they shifted to the BRRRR method (Buy, Rehab, Rent, Refinance, Repeat). Daniel discovered LendingOne when searching for a lender with a short seasoning period for refinancing distressed properties. “Everybody else was either six months to a year, and the fees and everything were pretty comparable… but you guys were the only ones I think would do a three-month seasoning,” he says.

Daniel has since completed close to 10 loans with LendingOne, praising the seamless experience with every transaction.

Overcoming Challenges: The Power of a Trusted Team

Managing 16 properties while maintaining a full-time job presents unique challenges, but Daniel emphasizes the importance of trust and verification. He works with three different property management companies and considers himself a “hands-on owner,” staying informed about every detail. “If something breaks, I want to know about it,” he insists, as this allows him to identify problems before they happen.

He’s faced everything from a tree falling on a house to multiple evictions during the COVID-19 pandemic. However, his success is largely attributed to his robust support network. His team includes a trusted contractor for flips, long-standing property management companies, reliable realtors, and even personal connections, such as his best friend and father-in-law, who provide on-the-ground support when he’s not physically present.

The End Goal: Financial Freedom and Beyond

Daniel and his wife set annual investment goals, initially focusing on acquiring properties and doing flips. Their ultimate objective is to transition out of their W-2 jobs and live off their rental income.

Their current cash flow target is $12,000, a figure adjusted from an initial $10,000 to account for the inevitable 20% that goes towards maintenance and unexpected issues. While there’s no fixed “end number” of properties, Daniel acknowledges the “addictive” nature of their investment journey. “We need to take a break and not do anything,” he says of their conversations, “And then that lasts like a week, and then we’re looking at other properties.”

Advice for Aspiring Investors

For those just starting in real estate investing, Daniel offers straightforward advice:

  • Learn to analyze properties: Understand the numbers and potential returns.
  • Maintain adequate reserves: Account for unexpected expenses and vacancies.
  • Build a trusted team: Surround yourself with reliable professionals who share your goals.

Daniel’s story is a testament to the power of a clear vision, strategic action, and the importance of building a strong support system. His journey exemplifies how initial hesitation can evolve into substantial success with the right approach and partnerships, demonstrating that financial freedom through real estate is a realistic goal.