How A Full-Time Pilot Closes $1.6M In Milwaukee Single-Family Rentals

Send us Fan MailTwenty closings in a week sounds like chaos until you see the structure behind it. I’m Cole, a legacy airline pilot and military instructor pilot building a Milwaukee real estate portfolio on nights, weekends, and whatever layovers give me. This update breaks down a seven-day sprint that includes Blackhawk flights, my first Boeing 777 run from New York to Paris and back, and nearly $2 million in single-family rental purchases.I walk through two very different deals. First, five stabilized houses on the same street, already generating over $10,000 a month in gross rents, bought for about $600,000 with a seller credit and a hard reminder that lenders still want skin in the game. Then I unpack the long, messy 15-home portfolio I’ve negotiated for two years: small houses with deferred maintenance, vacancies, unpaid taxes, and liens, but a clear value-add path with a targeted rehab budget and realistic rent expectations.We also get practical about financing and risk. I explain why hard money can be the right tool when speed matters, what a cash-out refinance can and cannot return at typical 75% LTV limits, and how I think about exit strategies like holding for cash flow, selling, or using a 1031 exchange. If you’re trying to build rental property income while keeping a full-time job, I share the “boring” factors that actually unlock growth: credit, consistent income, and hiring a solid property manager early.Subscribe for the closing statements and the full numbers, share this with a friend trying to buy their first rental, and leave a review if the behind-the-scenes detail helps. What part of this process feels hardest for you right now?