BiggerPockets Real Estate Podcast: Episode 2025 – Long-Distance Investing Blueprint (Listen Before Buying)
Release Date: July 9, 2025
Hosts: D. Dave Meyer and Henry Washington
Duration: Approximately 38 minutes

Introduction

In Episode 2025 of the BiggerPockets Real Estate Podcast, hosts D. Dave Meyer and Henry Washington delve into the intricacies of long-distance real estate investing. Aimed at empowering investors to achieve financial freedom through strategic property acquisitions away from their home markets, this episode serves as a comprehensive guide for those considering expanding their investment horizons.

Choosing the Midwest: A Strategic Decision

Timestamp [00:00 – 05:37]

The episode kicks off with Dave and Henry announcing their upcoming Midwest Cash Flow Roadshow, focusing on Milwaukee, Chicago, and Indianapolis. Their choice of the Midwest is underpinned by a combination of affordability, strong rental markets, and robust economic indicators.

Key Points:

• Affordability Meets Opportunity:
  Dave emphasizes Chicago's affordability compared to other major cities, noting, "Median home price in Chicago is $350,000. Find me another major city with an economy like Chicago that has price points like that" ([05:29]).

• Economic and Infrastructure Strength:
  Henry highlights the economic symbiosis between major cities and their suburbs, stating, "there's just a lot of economics and infrastructure that make for what could potentially be a good real estate market" ([04:38]).

• Cash Flow Potential:
  The duo discusses how the Great Lakes region presents a "perfect storm" for cash flow, combining affordable home prices with strong rental incomes and job growth ([04:38]).

Planning the Cash Flow Roadshow

Timestamp [02:01 – 03:23]

Dave outlines the logistical aspects of their roadshow, detailing their itinerary from Milwaukee to Chicago and finally Indianapolis. He underscores the importance of efficient planning to maximize the trip's productivity.

Key Points:

• Itinerary Strategy:
  The chosen corridor between Milwaukee and Chicago offers a blend of major city dynamics and smaller, affordable markets within a manageable driving distance ([03:23]).

• Event Invitations:
  Listeners in the Great Lakes region are invited to free meetups in Chicago and Indianapolis on July 15th and 16th, respectively, fostering community engagement and networking opportunities ([02:38]).

Building Your Long-Distance Investment Team

Timestamp [06:36 – 19:37]

A significant portion of the episode is dedicated to assembling a reliable local team—an essential factor for successful long-distance investing.

Key Points:

• Importance of a Local Team:
  Henry stresses, "real estate investing is a team sport" and highlights agents and property managers as crucial components ([06:43]).

• Interviewing Agents:
  Dave advises interviewing multiple agents to gauge their market understanding without revealing specific investment parameters initially. He shares a strategy of asking agents, "if you were me and you had unlimited time and money, what would you invest in?" to assess their expertise ([14:12], [15:20]).

• Notable Quotes:

  • Henry on agent communication: "If you don't have good communication, then details get missed, deals get lost" ([13:35]).
  • Dave on agent success stories: "Show me success stories of your clients in the market... it teaches you so much" ([17:44]).

• Property Manager Insights:
  Henry offers a bonus for listeners—a list of 25 questions to ask potential property managers, emphasizing the need for proactive management and alignment with the investor’s philosophy ([19:37]).

Evaluating Neighborhoods: Beyond the Numbers

Timestamp [24:00 – 34:19]

The hosts transition to discussing how to assess neighborhoods effectively during their roadshow.

Key Points:

• Pre-Trip Research:
  Investors should identify potential neighborhoods based on data and seek agents' recommendations for additional areas ([27:27]).

• On-the-Ground Evaluation:
  Henry advises visiting neighborhoods at different times, including evenings, to get a true sense of safety and community dynamics ([27:11], [28:38]).

• Strategic Alignment:
  Depending on investment goals—whether seeking established desirable areas or emerging "path of progress" neighborhoods—investors should tailor their neighborhood evaluations accordingly ([29:33], [30:00]).

• Housing Stock Quality:
  Dave underscores the importance of assessing the overall quality of housing in a neighborhood, not just individual properties, to gauge potential appreciation and tenant appeal ([31:27]).

Final Tips and Best Practices

Timestamp [34:25 – 37:35]

As the episode nears its conclusion, Dave and Henry offer additional strategies to optimize long-distance investing endeavors.

Key Points:

• Community Engagement:
  Attending city council meetings, chamber of commerce gatherings, and local investor meetups can facilitate valuable connections and insights ([35:46], [36:26]).

• Seasonal Visits:
  Visiting markets during off-peak seasons like spring or fall allows investors to experience neighborhoods beyond their best days, avoiding deceptive impressions that could arise from touring only during peak seasons ([35:47], [37:16]).

• Operational Considerations:
  Henry reminds investors to account for local operational costs, such as snow removal in colder climates, which can impact profitability ([37:35]).

Conclusion and Call to Action

Timestamp [37:52 – End]

Dave and Henry wrap up the episode by reiterating the value of their Midwest roadshow and encouraging listeners to join their upcoming free meetups in Chicago and Indianapolis.

Key Points:

• Join the Roadshow:
  Listeners are invited to attend the free Cash Flow Roadshow events in Chicago on July 15th and Indianapolis on July 16th by RSVPing at biggerpockets.com/roadshow.

• Stay Connected:
  For further questions or personalized advice, listeners are encouraged to reach out via BiggerPockets or Instagram, fostering a supportive community for real estate investors.

Key Takeaways

1. Strategic Market Selection:
   Choosing markets like Milwaukee, Chicago, and Indianapolis offers a blend of affordability, strong rental demand, and economic stability.

2. Assembling a Reliable Local Team:
   Prioritizing communication and investor experience when selecting agents and property managers is crucial for long-distance success.

3. Thorough Neighborhood Evaluation:
   Combining data-driven research with on-the-ground assessments ensures informed investment decisions.

4. Community Integration:
   Actively participating in local events and meetings can unveil hidden opportunities and streamline investment operations.

5. Operational Readiness:
   Understanding and planning for local operational costs and seasonal challenges can safeguard investment profitability.

By following the blueprint outlined in this episode, aspiring long-distance investors can emulate the strategies of seasoned professionals, positioning themselves for sustained success in diverse real estate markets.