How Im Investing In Real Estate Right Now (Despite High Prices)

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Ever feel like you've done everything right in your career but still can't afford the home you want? You're not alone. As a commercial airline pilot, military instructor, and real estate investor, even I'm feeling the squeeze of today's housing market—so much that I'm currently renting an apartment while owning multiple rental properties.
My response? A contrarian investment strategy focused on properties many investors overlook. I'm targeting homes in Milwaukee's $100,000 range (plus or minus $20,000) that offer immediate cash flow while positioned for substantial appreciation. These aren't Instagram-worthy properties, but they might be the smartest plays in today's market.
The thesis behind this approach is what I call the "waterfall effect." As buyers get priced out at the top of the market due to inflation, interest rates (currently at 7.5%), and skyrocketing property taxes (mine increased 30% last year), they're forced to look at the next tier down. This creates a domino effect through every market segment, eventually driving up demand in previously overlooked neighborhoods. I've already seen this play out in Milwaukee's south side, where similar properties have experienced explosive growth.
My recent purchases—a $68,000 single-family home and a $112,000 duplex—exemplify this strategy. While not exciting, these properties cash flow nicely while offering potential 50-100% appreciation as market pressures intensify. The kicker? You couldn't rebuild these homes for anywhere near their purchase price today, suggesting they're fundamentally undervalued.
What makes this approach powerful is its built-in safety net. If my appreciation thesis proves wrong, I'm still generating positive cash flow and building equity through debt paydown. But if I'm right, these "boring" investments could deliver extraordinary returns as middle-class buyers increasingly find themselves with no other options.
Are you seeing similar market pressures where you live? Join the conversation and share your experiences—I'd love to hear how you're adapting your investment strategy for 2025 and beyond.

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1. Introduction and Investment Strategy (00:00:00)