Real Estate Rookie Podcast Episode Summary

Episode Title: Cash Flow vs. Appreciation Markets: Which We’d Choose (Rookie Reply)
Date: September 5, 2025
Hosts: Ashley Kehr, Tony J. Robinson
Podcast: Real Estate Rookie (BiggerPockets Podcast Network)

Overview

This episode focuses on practical, rookie-level real estate investing questions, with a deep dive into how to pick the right market as a beginner. Hosts Ashley Kehr and Tony J. Robinson offer honest, experience-based guidance on navigating relationships with property managers, the classic debate between investing for cash flow versus appreciation, and best practices for pricing and marketing your rentals in a competitive market.

Key Discussion Points & Insights

1. How Many Bids Should You Get for Rental Repairs?

Question from Oscar: Is it unusual to request multiple contractor bids from your property manager?

• Ashley’s Perspective:

  • Three-Bid Standard: When managing, anything over $5,000 gets three bids; small jobs (e.g., $200 plumbing fix) do not (01:16).
  • Pushback Is Common: Managers may resist getting multiple bids due to preferred vendor relationships (sometimes with ownership interests).
  • Benefit to Owners: Established relationships with vendors can lead to prioritized service and discounts—balance this with your need for transparency.
  • Stick to Your Request: If you feel strongly, keep pushing for bids unless your management agreement clearly states otherwise (03:47).

  “If you want multiple bids, go ahead, like, keep pushing for it. Like, don't give up unless, you know, it clearly does state in the property management agreement that you signed that, that they actually don't do that.”
  — Ashley (06:10)

• Tony’s Perspective:

  • Some PMs Have In-House Repair Crews: PMs may require you to personally source outside bids, so clarity up front about these policies is crucial (03:47).
  • Ask About Thresholds and Processes: Get clear on the dollar thresholds at which bidding occurs, and put this in writing.
  • Small Expenses Add Up: Little ongoing costs for maintenance can seriously erode cash flow; always audit these recurring charges (06:30).

  “Sometimes we think about saving money as an investor in big capital expenses, but oftentimes it comes down to these little leaky holes... That’s how you end up with more money at the end of the year.”
  — Tony (06:36)

Memorable Segment (10:15): The team riffs on the pain of finding reliable handymen and jokes about the need for an “Uber for tradespeople”—Tony calls it a “billion dollar idea” (11:33).

2. Cash Flow vs. Appreciation: Which Should You Target First?

Question from Sean: Should I pursue BRRRR strategy in Detroit for cash flow, or appreciation in Tampa (with potential for short-term rentals)?

• Tony’s Recommendation:

  • Clarify Your Main Goal: Cash flow and appreciation are rarely found in full strength in one market; decide which matters based on your immediate needs and long-term plan (15:39).
  • For Early Financial Freedom: Cash flow is often the better choice if quitting your job in 5 years is the goal.
  • BRRRR for Capital Recycling: You can snowball your portfolio faster by recycling capital and layering in strategies like mid-term or room-by-room rentals (16:18).

  “What’s most important is what aligns best with what it is that you want... both of those strategies could work... But it’s which one you can execute better.”
  — Tony (19:10)

• Ashley’s Recommendation:

  • Analyze the Numbers—Not Just Hopes: Run numbers for both cash flow and potential appreciation; consider all benefits including tax (cost segregation, bonus depreciation) (17:05).
  • Long-Term Wealth Tilt: Ashley’s own experience: Properties that have strong appreciation—even with less cash flow—have outperformed pure cash flow properties over a 10-year span (18:13).
  • Appreciation-First Play: Especially useful for those planning to 1031-exchange into bigger properties later.

  “Looking back in the 10 years I’ve been investing, I would pick the appreciation play over more cash flow every day."
  — Ashley (18:18)

3. Rental Not Leasing Out—When to Lower the Price?

Question from Kyle: Rental property listed on Zillow gets lots of views but only one inquiry after four days. When should rent be lowered?

• Ashley’s Advice:

  • Don’t Panic Early: Four days is not long enough. She’s had units sit for weeks or even a month; patience and the right tenant matter more than speed (25:01).
  • List Conservatively: Always lists slightly under market value to secure more applicants and gives flexibility for rent increases later.
  • Optimize Marketing: Expand to other listing sites (e.g., Facebook Marketplace) and make ad copy as descriptive and helpful as possible to attract the right tenants (28:42).

  “Just because there's not a ton of showings doesn't mean that the right person isn't out there... You just need the right person to see the property.”
  — Ashley (26:07)

  • Comprehensive Info in Listings: List all amenities, utilities, proximity to points of interest, pet policies, fees, and flexible contact methods (phone, form, etc.) to reduce screening friction (29:50).

• Tony’s Advice:

  • Numbers Over Emotion: Run the math—being vacant for a month can cost far more than a small rent reduction (32:14).
  • When to Lower Rent: Around the 30-day mark, consider a rent drop. Remove and re-list with more detail and fresh photos to reset interest (33:23).
  • Screen Well at Lower Rents: Lowering price could bring applicants for whom rent is a stretch—tighten your screening to avoid downstream problems (33:23).

  “If you’re empty for 30 or 45 days, you just racked up almost $3,000 of cost for yourself to cover that mortgage to save yourself $600. Right. That’s a losing equation.”
  — Tony (32:54)

• Resource Plug: Ashley mentions her resource hub for tenant screening and due diligence at biggerpockets.com/rickeyresource (35:16).

Notable Quotes

• On pushing for multiple repair bids:
  “Preferred vendors of the property management company most likely are going to make the properties of the property manager a priority… But that could be a part of it—if you want multiple bids, go ahead and ask.”
  — Ashley (02:27, 03:41)

• On the cash flow vs. appreciation decision:
  “It’s very rare that you find a market that gives you an equal dose of both of those...What is more important to you right now?”
  — Tony (15:44)

• On patience in rental leasing:
  “Be patient because I have had properties sit for 30 days waiting for somebody. I’ve had it sit for a week...you just need the right person to see the property.”
  — Ashley (25:37)

• On the pain of finding reliable handymen:
  “No one has really solved that challenge... If you can solve that issue, you’d have a line of people banging down your door.”
  — Tony (10:15)

Timestamps of Key Segments

| Timestamp | Segment Topic | |--------------|---------------------------------------------------------------------| | 00:23-06:30 | Getting multiple repair bids from property managers | | 06:30-11:55 | Handling small maintenance/handyman issues & “Uber for handymen” | | 14:04-19:10 | Cash flow vs. appreciation markets – which is better for a rookie? | | 24:11-35:16 | Pricing rental units, marketing tips, when/if to lower rent |

Conclusion

The hosts emphasize the importance of aligning real estate strategies with your personal financial goals, getting clarity on property management arrangements, and being systematic about marketing your rentals. For rookies, the takeaways are clear: ask questions proactively, analyze real numbers (not just theories), be patient with the process, and leverage resources and community knowledge for each step of the journey.

Resource Plug:
Ashley’s free tenant screening and real estate checklists: biggerpockets.com/rickeyresource

Next Steps:
For further guidance, subscribe to Real Estate Rookie or join the BiggerPockets Rookie forums.