Making $25,000/Year Cash Flow by Buying the Worst Rental on the Best Block

BiggerPockets Blog
Published: January 12, 2026
Growth & Marketing

Summary

This article discusses an investor who bought a run-down property in a desirable area and turned it into a successful short-term rental. Hosts can learn from the story about the importance of location, embracing renovation projects, and leveraging marketing skills for STR success.

Key Insights

  • The property was purchased sight unseen over FaceTime due to the favorable price and location, highlighting the importance of quickly assessing deals.
  • The investor used their marketing background to create a short-term rental with a focus on providing exceptional experiences for guests.
  • The investor's initial long-term rental in Chicago generated $800/month in cash flow, demonstrating the potential of a well-located property.

Action Items

  • Consider investing in a property in a desirable location, even if it requires renovations.
    Effort: medium
    Impact: high
  • Use your existing skills, such as marketing, to differentiate your listing and create a better guest experience to boost occupancy and revenue.
    Effort: low
    Impact: medium

Tools & Resources

  • Steadily: The article mentions Steadily, the landlord insurance company.
  • The Real Estate Rookie Podcast: The article mentions The Real Estate Rookie Podcast.
  • New Western: The article mentions New Western, a company specializing in wholesaling properties.

Common Mistakes

  • Overestimating renovation costs can lead to financial challenges.

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