Podcast Summary: Real Estate Rookie (BiggerPockets)

Episode: Pay Off Properties or Buy More with Mortgages? (Rookie Reply)
Date: September 26, 2025
Hosts: Ashley Kehr and Tony J. Robinson

Episode Overview

In this “Rookie Reply” episode, Ashley and Tony answer three of the most pressing questions facing new real estate investors:

1. Should you pay off properties or scale with leverage?
2. Is house hacking still viable if you don’t want roommates?
3. What’s harder when starting out—finding deals or securing financing?

Their candid, practical discussion—laced with personal stories and actionable insights—helps new and aspiring investors navigate these major decision points.

1. Should You Pay Off Properties or Buy More with Mortgages?

Balancing Dave Ramsey’s anti-debt advice with the power of leverage in real estate investing

Key Points and Insights

• Dave Ramsey’s Approach: Dave Ramsey preaches that all debt is bad and only condones paying cash for investment properties ([00:32]–[01:35]).
  • Tony summarizes: “Dave basically says that all debt is bad debt, no matter what the circumstance, and you should never have debt.” ([00:44])
• Personal Experience with Debt Freedom:
  • Ashley shares: “I was a Dave Ramsey fan...I paid off farm equipment debt, a home equity line, and my student loans.” ([01:35])
  • However, as an investor, Ashley believes there’s no one-size-fits-all, as investing is emotional and depends on your stress tolerance.
• Running the Numbers:
  • Ashley advises to “run the numbers and look, okay, if you had that $500,000 property and you held it for 10 years, what would be your cash flow?...If you took that money and bought five properties?...At least use the numbers as a starting point.” ([02:46]–[03:37])
  • Important to account for more assets meaning more management, overhead, and complexity.
• Leverage as a Tool:
  • Tony notes: “Leverage is one of the tools that makes real estate investing so attractive...You get to control an asset that’s worth half a million dollars with only 10, 20, 30% down.” ([04:53])
  • Suggests a blend: “If you’re concerned about overleveraging, maybe set a rule...I’m going to be at no more than 70% loan to value.” ([04:45])
• Life Stage Considerations:
  • Younger investors may accept more leverage; older investors might prioritize capital preservation.
  • Tony: “Maybe buying more properties in cash or putting them on a 15-year note makes more sense if you’re closer to that timeframe in your life.” ([05:44])
• Bottom Line:
  • There’s a spectrum between aggressive leverage and absolute debt avoidance. Figure out what fits your risk tolerance, life stage, and practical management ability.

Notable Quotes

• “Investing can be emotional...If you’re not sleeping at night even though you’re making a great return, that’s not exactly a healthy lifestyle.” – Ashley ([02:09])
• “It’s more of a sliding scale than a black or white...There’s a middle point here.” – Tony ([05:14])

2. House Hacking Without Roommates—Is It Still Viable?

How to reduce your housing costs without sharing your personal space

Core Question:
A couple wants to house hack (offset living costs by renting out part of their residence) but doesn’t want to rent by the room due to past roommate experiences. They're interested in options for separate living spaces in the $400k range near Raleigh, NC. ([09:18])

Key Discussion Points

• Defining Success in House Hacking:
  • Ashley reframes: “The goal of house hacking is really to offset your own cost of living. If you can cash flow, that’s great...But don’t get strung up that it’s not a deal if you’re just saving money on housing.” ([10:48])
• Expanding the Strategy Beyond Room Rentals:
  • Tony: House hacking doesn’t just mean renting rooms. Consider:
    • Renting out a finished basement with a separate entrance
    • Building or purchasing a property with an ADU (Accessory Dwelling Unit)
    • Buying a duplex, triplex, or fourplex and living in one unit
  • “One solution is just expanding your buy box to potentially identify other types of structures that would allow you to house hack while keeping your space separate.” ([12:14])
• Short-Term and Mid-Term Rentals:
  • Ashley: Consider renting out “the other unit” on a short- or mid-term basis for extra flexibility—like during holidays or family visits ([13:13]).
• Screening Tenants for Peace of Mind:
  • Tony asks Ashley for advice on better roommate selection:
    • If it's your primary residence, you legally have more discretion over who lives with you ([14:26])
    • Screen thoroughly: use tenant screening tools (TurboTenant, RentRedi), run background checks, review social media.
    • “You should be doing social media...Looking at their Facebook profile—does it give you an idea of how they would treat your home?” – Ashley ([15:38])
• Real-Life Anecdotes:
  • Humorous story about screening tenants via TikTok, demonstrating the value of online background checks ([16:49]).

Notable Quotes

• “As long as you are decreasing your living expenses, or moving to a bigger property you couldn’t afford without someone supplementing income...that’s a win.” – Ashley ([11:11])
• “You can probably head off a lot of issues with the right screening upfront...Just really take your time.” – Tony ([17:25])

3. What’s Harder for Rookies: Finding Deals or Securing Financing?

Breaking down the classic “chicken or egg” dilemma for new investors

Key Discussion Points

• Chicken and Egg:
  • Ashley: “What came first, the deal or the financing?” For her, it was a money partner “who was interested,” then she found the deal ([23:25]).
  • Tony: “My first deal, the financing came first and that was what pulled me into that market.” ([24:07])
• It Depends on Market & Personal Traits:
  • Market Factors: “Sometimes finding good deals is easier than other times.” When rates were super low (2021-22), deals were easier; now, tight inventory and high rates make good deals scarce. ([24:37])
  • Personal Factors: Outgoing personalities may find deal sourcing easier; others may be more comfortable arranging financing.
• Current Market Analysis (2025):
  • Financing is easier than before—variety of creative options, and more sellers are open to terms like seller financing ([27:02]).
  • Properties are sitting longer on the market, especially those needing fixes or from mom-and-pop landlords ready to retire.
  • “I just got emailed by one [landlord]...Has like five properties he wants to sell...wants some kind of creative finance deal.” – Ashley ([27:40])
• Ultimate Answer:
  • Both are essential: “It doesn’t matter what’s harder...You’ve got to do both.”
  • Leverage expertise: If you’re weak at deal finding, enlist agents or wholesalers; if lending is toughest, get help from brokers or partners ([26:21]).

Notable Quotes

• “It doesn’t matter what’s harder...It’s just, ok, which one do you need help with first?” – Tony ([26:45])
• “Right now it’s easier to get the financing...I think getting creative and different options will make financing a little bit easier.” – Ashley ([27:02])

Timestamps for Major Segments

• 00:32 – Dave Ramsey vs. Leverage for Investors
• 01:35 – Ashley’s Personal Experience Paying Off Debts
• 04:06 – Tony on Finding a Middle Ground with Leverage
• 09:18 – House Hacking Without Roommates: Options and Advice
• 12:05 – Creative House Hacking Strategies
• 14:26 – Screening Tenants When House Hacking
• 23:25 – Which Is Harder: Finding Deals or Financing?
• 27:40 – Market Trends: Deals, Financing, and the Future

Memorable Moments

• Ashley’s spreadsheet “snowball tracker” and the emotional side of becoming debt-free ([01:35]).
• Tony’s pragmatic view: blending Ramsey with leverage depending on stage of life and goals ([05:44]).
• The story about a tenant’s TikTok, underlining the importance of background checks beyond the usual paperwork ([16:49]).
• The realistic acknowledgment that “you’ve got to do both” (deals and financing), so play to your strengths or partner for your weaknesses ([26:21]).

Conclusion

This episode equips rookie investors with real-world perspectives—balancing emotional and mathematical factors in debt, adapting house hack strategies to personal life circumstances, and tackling the deal vs. financing challenge. Ashley and Tony’s relatable stories and actionable advice provide reassurance and clarity for anyone taking their first (or next) real estate steps.