Steal This Process to Find the Best Real Estate Market with John Casmon, Ep. 770

Written by John Casmon

December 10, 2025

This episode features a solo session with John Casmon, where he draws on personal investing experience in markets like Chicago, Cincinnati, Louisville, and San Antonio to share a deep-dive framework for evaluating which markets to invest in, and how to spot the signs of long-term growth. From understanding economic indicators and infrastructure to aligning your personal investing style with neighborhood dynamics, this episode is packed with strategic guidance on identifying the right market — and the right moment — to make your move.


Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.


Key Takeaways

  • Start by investing in your own backyard, local familiarity and access outweigh national trends early on.
  • Use “path of progress” logic to spot adjacent neighborhoods with similar fundamentals but lower prices.
  • Look for population growth, industry diversification, infrastructure investment, and pro-development policies.
  • Understand your own investing goals to determine what kind of markets and submarkets align with your criteria.
  • Ride the coattails of developers and large employers, when they commit to a market, opportunity follows.


Topics

Why Market Selection Matters

  • Why investing close to home gives you an advantage
  • How John evaluated neighborhoods like North Center, Avondale, and Hermosa in Chicago

Expanding Beyond Your City

  • Lessons from shifting to Cincinnati and using family ties to anchor new market exploration
  • The importance of clarity on investor criteria before analyzing new areas

What Makes a Market Attractive

  • Key indicators: population growth, job diversity, geographic accessibility
  • Red flags: rent control, oversupply, misaligned development

Case Studies: Cincinnati, Louisville, San Antonio

  • The impact of infrastructure and corridor development in Cincinnati
  • How recession-resistant industries shaped John’s decision to invest in Louisville
  • Why San Antonio’s “quiet strength” made it a strategic move

Using Public Data to Guide You

  • Sites John uses: census.gov, bls.gov, datausa.io
  • How to track local chambers of commerce, development plans, and funding incentives

What to Avoid or Watch Closely

  • Risks of relying on government subsidies or unstable funding
  • Importance of local political climate and long-term planning by municipalities


📢 Announcement: Learn about our Apartment Investing Mastermind here.


Next Steps

  • Research your backyard market before expanding elsewhere
  • Align your criteria (cash flow vs. appreciation, investor type) before evaluating a market
  • Track macro indicators (population, jobs) and micro conditions (local policy, neighborhood dynamics)


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