Real Estate Rookie I Built a Rental Portfolio That Gives Me “Boring,” Steady Cash Flow
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Nov 10, 2025 Esther Simeone, a digital marketing director turned real estate investor from Los Angeles, shares her inspiring journey into real estate despite battling a competitive market. She discusses the power of persistence, recounting how she submitted 15 offers before finding an overlooked property. Esther explains her creative strategies, including rental arbitrage and midterm rentals, to create steady cash flow. She even designed an ADA-accessible vacation rental, blending purpose with profit while showcasing the potential of accessible spaces in today's market.
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Hidden Duplex Opportunity Turned Cash Flow
- Esther found a cabin-like Los Angeles listing with hidden 900 sq ft space above the garage that others overlooked.
- She bought it, converted the space into a rentable guest house, and house-hacked to cover ~60% of the mortgage.
Check Old Listings For Hidden Value
- Don’t dismiss listings that sit; investigate why they’re overlooked since cosmetic issues or poor marketing often explain it.
- Focus on deal fundamentals and what you can change rather than listing age or first impressions.
Use DIY Skills To Reduce Rehab Costs
- Learn basic rehab skills and DIY where feasible to save costs; use YouTube and practice on small projects.
- Track weekly progress to stay motivated while balancing a full-time job and renovations.