Real Estate Rookie Podcast: How to Buy Cash-Flowing Rentals in 2026 (Despite High Rates) (Rookie Reply)

Hosts: Ashley Kehr & Tony J. Robinson
Release Date: January 9, 2026
Podcast: Real Estate Rookie (BiggerPockets)
Episode Goal: To answer listener questions on how new investors can navigate high interest rates, learn key skills, and optimize taxes to still build cash-flowing rental portfolios in 2026.

Episode Overview

Ashley and Tony answer three common rookie investor questions:

1. Is cash flow still possible with high rates, and what's the best financing strategy for beginners?
2. What job or experience best prepares someone for real estate investing?
3. What should new investors ask their CPA to maximize tax benefits and avoid common pitfalls?

Their tone is practical, encouraging, and candid, aiming to reassure rookies that real estate investing is still possible—and profitable—with smart adjustments and planning.

1. Is Cash Flow Still Possible with High Interest Rates? (00:34–11:01)

Question:
Ray from the BiggerPockets forums worries that high rates make cash flow impossible and wonders about using a HELOC or Roth IRA to fund rentals.

Main Points

• Markets & Strategies Matter More Than Ever

  • Tony: Blanket statements like "cash flow is dead" ignore the differences between markets and strategies.
  • Real example: An investor in Philadelphia using buy-and-hold with Section 8 tenants is still netting ~$1,000/month per duplex (02:50).
  • Quote — Tony (02:55):

    “So the question isn’t ‘Can I get cash flow?’ The question is ‘What market, what strategy, what niche should I be focused on?’ ...it’s the combination of those things that’ll help you find the cash flow.”

• Look at All the Benefits, Not Just Monthly Cash Flow

  • Ashley: Cash flow isn’t the only measure of success—consider appreciation, tax advantages, mortgage paydown, etc.
  • Rental income is taxed differently; you can leverage things like cost segregation, the short-term rental loophole, and real estate professional status to keep more money in your pocket now.
  • Quote — Ashley (06:10):

    “What if that same exact property could actually decrease you not having to pay $20,000 in taxes that year? ...That’s a little over $1,000 a month back in your pocket that you’re not paying in taxes… That’s what took me a long time to realize.”

• Adjust Your Expectations for Cash Flow

  • Both hosts say that the days of 1–2% rule deals are rare. If properties break even or yield modest cash flow but come with long-term gains, they can still be valuable.
  • Ashley: Her highest-cash-flowing properties often had management headaches. Over time, appreciation and mortgage paydown added even more wealth.
  • Tony: Their return expectations have shifted from annual revenue = 30% of purchase price, down to 15–20% due to doubling rates since he started.
  • Quote — Tony (09:30):

    “The people who say now is not a good time to buy are probably never going to get started... The right time is always ‘how can I adjust my strategy and expectations to the current market?’”

Key Takeaway:
Yes, cash flow is possible in 2026—but you must target the right markets, use creative financing, and appreciate the full benefits of real estate ownership, not just monthly profit.

2. What Job Best Prepares You To Be a Real Estate Investor? (13:23–24:37)

Question:
Taylor, a teacher, is moving to Birmingham and asks what job (acquisition analyst, property management, etc.) will build the skills to become a full-time investor.

Main Points

• Ashley’s “Hot Take”: Get the Highest-Paying, Most Flexible Job

  • You don't need a real estate job to learn how to invest; prioritize income and flexibility, which you can then leverage to fund deals and learn as you go.
  • Teaching offers good pay and excellent time off for investing.
  • Part-time side gigs in real estate (leasing, maintenance, shadowing) can build skills without sacrificing stable income.
  • Quote — Ashley (14:53):

    “I don’t think you need to learn a skill set to actually invest… You are just as capable learning online from home.”

• Tony’s Counter: If You Have a Financial Safety Net, Go All-In

  • Because Taylor’s wife earns a high income, Tony recommends getting a “risky” real estate job—like working for a top wholesaler—to learn how to find deals.
  • Quote — Tony (19:02):

    “If I were in his position, I’d try to find the biggest wholesaler in my market and go work for them... The ability to find a good deal is foundational for every investing strategy.”

• What’s the Most Useful Skill or Experience for Rookies?

  • Acquisitions (finding deals) and property management (running rentals) are both valuable, but success depends on your personality and goals.
  • Ashley: Being handy (maintenance/rehab) can save money, reduce fear, and empower new investors to control their projects.
  • Asset management (overseeing your investments as a business) may be even more valuable than day-to-day management.
  • Both: Know yourself—play to your interests, strengths, and the type of investing you’ll actually enjoy rather than following a preset path.

Key Takeaway:
There’s no single “best” job; maximize income and flexibility, and supplement with experience where possible. Skills in deal finding, property management, or handy work all help, but self-awareness and a supportive job situation are most important.

3. Navigating Real Estate Taxes: What Should You Ask Your CPA? (27:08–34:56)

Question:
Daniel has W-2 income and three rentals. He wants to ensure he isn’t missing tax savings by doing his taxes alone and asks what he should discuss with a CPA.

Main Points

• Choose a Real Estate-Savvy CPA

  • Tony: The most important question: “What percentage of your client base are real estate investors?”
  • Avoid CPAs you have to educate; they should bring proactive strategies to the table.
  • Quote — Tony (28:25):

    “You don’t want to get into a position where you’re educating your CPA... For me that would be my first question.”

• Self-Education Is Crucial

  • Use resources (e.g., BiggerPockets books by Amanda Han and Matt MacFarland) to understand enough to ask smart questions and recognize missed opportunities (like cost segregation).
  • Ashley (30:00):

    “I worked with the CPA for a long time that never told me about cost segregation. Now I know to ask, ‘how many cost segregation studies have you done for clients?’”

• Ask About Entity Structure and Planning

  • Keep rentals (passive income) and flips/wholesales (active income) in separate entities; reduces risk and tax burdens.
  • Ask your CPA to review your future plans (flipping, selling, holding, 1031 exchanges, etc.) so advice is strategic, not just reactive.
  • Tony (31:10):

    “Share with your CPA not only where you are now but where you’re going so they can advise you on making the right moves.”

• Consider Multiple Advisors

  • Use both a tax preparer and a strategic tax planner. One files, one helps optimize your tax position.
  • Ashley (32:29):

    “You don’t have to rely on just one person. And it really helps having two because if there is something that one brings up, you can talk to the other about.”

• Prioritize Frequent Communication—Don’t Wait for Tax Season

  • Aim for at least quarterly check-ins to plan and adjust throughout the year. It’s too late to save on last year’s taxes after December 31.
  • Quote — Tony (34:30):

    “How often are we meeting during the year? …If you’re waiting until April, it’s too late to really change much.”

Key Takeaway:
Proactively seek out tax professionals who understand real estate, learn enough yourself to ask sharp questions, and make tax strategy a year-round habit—not just a spring afterthought.

Memorable Quotes & Moments

• Tony on filtering advice (10:35):

  “If the folks who are telling you ‘don’t buy real estate’ are people who’ve never bought real estate… you gotta kind of filter that advice out.”

• Ashley’s “aha” moment (07:53):

  “I was like in shock when I just looked at this property I bought in 2017 and what it’s worth now… So much more value than just the cash flow.”

• Both on personality fit (22:40 & 23:43):

  Ashley: “For me, property management gave me the confidence… But it’s so easy to hire a property management company, so maybe asset management is the best answer.”

  Tony: “For me, I’m good at property management, but I don’t like it.”

Timestamps for Key Segments

• 00:34 – Ray’s cash flow question: is investing still worth it?
• 02:50 – Real example of cash-flowing rentals in tough markets
• 04:12 – Real estate vs. stock market: broader investing benefits
• 06:52 – Ashley’s cash flow journey and shifting expectations
• 08:55 – Tony’s evolving cash flow benchmarks and “right time to buy”
• 13:23 – Taylor’s career change & experience-building question
• 14:53 – Ashley: Why more income/flexibility > “real estate job”
• 19:02 – Tony: When a side gig in acquisitions makes sense
• 22:40 – What skills/roles set new investors up for success?
• 27:08 – Daniel’s tax prep question: finding a savvy CPA
• 28:25 – Vetting professionals: “How much of your business is real estate investors?”
• 32:29 – The two-CPA approach: tax planning vs. preparation
• 34:30 – The necessity of year-round tax planning

Final Thoughts

• Investing in 2026 is challenging but far from impossible: If you adapt your expectations, master your market/strategy, and take advantage of all real estate's benefits, you can still build a profitable portfolio—even with higher rates.
• Learning by doing is still the best teacher: Self-education, strategic networking, and tailoring your real estate journey to your strengths and goals matter more than any one “right way.”
• Tax strategy should be proactive and frequent: Find real estate-literate advisors, self-educate, and stay in touch throughout the year to make the most of your deductions and planning.

Hosts Sign Off:
"Thank you guys so much for joining us today on Rookie Reply. I'm Ashley, he's Tony, and we'll see you guys on the next episode." (34:56)

For further resources, visit BiggerPockets.com, and consider Amanda Han and Matt MacFarland’s tax books as recommended by the hosts.