Seth Wilson knows that the devil is in the details, whether you are a real estate investor or a U.S. Air Force pilot. “It might not seem like the two connect at first,” admitted the Air National Guard pilot, owner of Sierra Whiskey Properties (SWP) and a recently-published author.

He went on, “Both as a pilot and as a real estate investor, I would find myself in horrible situations – and when you’re getting started in either career, every crisis, major or minor, is horrible – and I would lie in bed at night trying to think about how to solve these challenges. I would always find the answer to the challenge I was facing in real estate somewhere in my military experience.”

Seth Wilson

Details Matter

Wilson described one particular incident that he later wrote about on his blog and that he decided to include in his book, “Real Estate Flight Plan: A Combat Pilot’s Guide to Navigating Real Estate Success.” He had purchased a property from an owner who had held it for the previous 10 years and had neglected a minor yet meaningful maintenance issue.

“He did not take care of the drainage. Every time it rained, water would dump at the foundation of the property,” Wilson said. The oversight led to serious foundation issues. “All the owner would have had to do was add about $200 in downspout extensions to get the water away from the building. Instead, he had to pay nearly $100,000 to have water-related repairs done before we closed,” said Wilson, noting that he also got a substantial discount on the property thanks to the issue.

The pilot compared the relatively minor expense of adding the downspout extensions and the major cost of failing to do so to a scary incident he experienced in Yuma, Arizona, thanks to another tiny oversight: the failure to flip one single switch. “That switch controls the hydraulics to the parking brake. It’s on the checklist. I had flipped it hundreds of times before,” Wilson recalled.

“When I started the engine in my plane without first flipping that switch, the airplane started to move when it wasn’t supposed to. It turned into a hairy situation because I didn’t flip that tiny little switch.” Little oversights can have huge consequences in real estate as well.

Starting Out with a Solid Battle Plan

When Wilson got started in real estate in 2009, he had little thought of getting into multifamily investing. “I started in mobile homes back in 2009 and was looking to start flipping houses, but I had no money and no experience,” he recalled. He developed a unique rent-to-own process for mobile homes.

“People who want to buy mobile homes don’t necessarily have the money for the cash down payment and they also cannot necessarily get a loan,” he said, attributing this common issue to many mobile-home buyers’ lack of credit and also to lenders’ lack of interest in “loaning $10,000 for a piece of personal property, which is what mobile homes technically are.”

Wilson solved that problem for mobile-home buyers and created his niche when he started buying mobile homes for cash. While he did not have a great deal of funding, these purchases were relatively small and, because he paid cash, he was often able to work with highly motivated sellers. “I gave my first seller $1,500 in cash. He signed the title over to me on the hood of his truck and that was the last time I ever saw him,” Wilson remembered. He continued to invest in mobile homes while he learned the necessity of having a complete “battle plan” for real estate. “You need a process to find the right property, market that property, negotiate the sale, and handle the paperwork,” he said.

Gaining Altitude 

Around the time Wilson solidified his real estate processes on that small scale, he was selected as a pilot in the Missouri Air National Guard. At the end of his initial training, he returned home to buy his first apartment building, called the Century Building. “It was a little 12-unit property, but it was a great success,” he said, adding that shortly thereafter investors approached him about purchasing and running first another 12-unit, then a 44-unit, and finally a 93-unit property. He has not slowed down since.

These days, Wilson focuses exclusively on garden apartments. The narrow focus enables him to snag great deals because he can often make same-day offers with confidence.

When Multifamily Housing Meets Military Precision

Wilson now leverages his unique perspective on real estate toward a single sector of the industry: multi-family housing. “We only do multifamily, and we focus on garden apartments: two- or three-storywalk-upss for the middle-market tenant,” he said. Because SWP has such a clearly defined focus, Wilson finds he can usually make an offer on a property that meets his requirements the same day that he encounters it because he knows that he will be able to fill any vacancies in short order thanks to a deep familiarity with his renting base.

“We know everything about that population: their shopping habits, where they like to live, where they work, what kind of amenities they want, and even how they prefer to pay their rent.” Wilson has programs for tenants who want to pay by money order, e-check, and more conventional methods like written checks and automatic withdrawals. “We make it as easy as possible for our tenants – our customers for all intents and purposes – to have a nice place and be able to pay us easily,” he said.

Always Looking to Level Up

Wilson attributes his company’s success to his focus on adding value to properties in his specific niche. “My favorite strategy is to invest in places that need love and attention, which really translates to money and management,” he said. “It’s not that there is anything terribly wrong with the property itself or the way that it is managed, but we really know exactly what our tenants want and give it to them. Because we bring that to the table, we can raise the rents and the valuation as well.”

Despite his fondness for process, Wilson is not one to simply repeat past successes without expanding his horizons. “We are always looking to do bigger and better deals, bigger and better things for our investors and tenants, really create win-win situations for everybody,” he said. “That may sound kind of cliché, but it’s important because if you don’t create benefit for someone else, they certainly won’t create benefit for you. Just keep on the trajectory.” Wilson and SWP are clearly still maintaining an upward one.

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  • Carole VanSickle Ellis

    Carole VanSickle Ellis serves as the news editor and COO of Self-Directed Investor (SDI) Society, a membership organization dedicated to the needs of self-directed investors interested in alternative investment vehicles, including real estate. Learn more at or reach Carole directly by emailing

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