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Webinar hosted by Jake Prieur (marketing lead) and Steve Navity (managing partner of Skyline Point Capital) introducing real estate—particularly multifamily—as a strategy to accelerate retirement and generate passive income. They frame the problem as four structural headwinds to retirement: insufficient stock-market returns, increased longevity weakening Social Security, CPI under-reporting of real inflation (they cite the Chapwood Index), and rising healthcare costs. The speakers argue multifamily real estate in Sun Belt markets (Dallas–Fort Worth, Nashville, Charlotte and nearby metros) provides lower volatility, multiple income streams (rent, ancillary income, appreciation), faster rent re-pricing, inflation-hedging, and strong tax benefits via cost segregation and bonus depreciation. Specific examples cited: 24-unit Empire Apartments (bought 2018 for $1.1M, sold 2022 for >$1.8M — described as a 4.4x gain with ~69% annual return), Lux at Indian Lake Village (94-unit Class A in Henderson/TN, bought Dec 2022 for $26M; $670k capex projected to add ~$3.8M value; converting amenity space into rentable offices added ~$1.2M in value at $700–$850/mo per office). A tax case study (“Dr. Sam Smith”) shows a $150k passive investment producing ~8% cash-on-cash (~$12k/yr) plus a first-year non-cash loss (~$121k) from bonus depreciation that offsets a $250k K-1, reducing taxable income and saving roughly $45k in taxes in the example. They outline a five-year portfolio-build scenario where repeated investments and tax-driven reinvestment can grow a portfolio toward ~$880k with increasing passive income.

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