805 episodios
- Is a cheap rental really the safest way to start, or does it just trade one risk for another? Plenty of new investors are asking the same question, especially when buying a rental property in their own market feels out of reach.
Welcome back to another Rookie Reply! Today, a house hacker earning $20 an hour has saved enough to buy his next deal without a mortgage, but only in a low-cost, Section 8, D-class area. Ashley also started out buying cheap duplexes, so she knows exactly what this path looks like! She shares the cash flow wins, the hidden headaches nobody warns you about, and the one move she wishes she’d made instead.
You’ll also hear how to budget for one of the most expensive systems in any older rental, and how a paid-off home can become the first step toward a portfolio that replaces your income! Plus, Ashley breaks down the long-game wealth-building moves most rookie investors forget to plan for!
Looking to invest? Need answers? Ask your question here!
In This Episode We Cover
Whether starting with a cheap rental is worth it
Using 20-year loans to build an entire portfolio of paid-off rentals
Why one better property can beat several cheap ones
How to budget for HVAC and ductwork before it becomes a $10K problem
Turning one inherited house into a rental-funded retirement income
And So Much More!
Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-796.
Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com.
Learn more about your ad choices. Visit megaphone.fm/adchoices - You could buy your next rental without a bank on terms you help write. That’s the power of seller financing, and it often opens up when high rates leave sellers short on options. Here’s how you can set up seller financing, and negotiate the terms to work in your favor!
Welcome back to the Real Estate Rookie podcast! Ashley and Tony have both bought with seller financing. Today, we’re showing you exactly how to structure a deal of your own. You’ll learn where to find sellers who are open to owner financing, the one follow-up question that can turn a seller’s “no” into a “maybe,” and why offering a higher price can actually get you a better deal on your next rental property.
From there, we’ll go through every lever you can negotiate: the price, rate, down payment, amortization, balloon payments, and prepayment penalties. We’ll walk through who pays the taxes and insurance, what happens if you miss a payment, and what to do if the seller (or their heirs!) wants out early. Plus, you’ll hear how to plan your refinance before the balloon comes due, and why your contract should come from an attorney (not an AI template).
In This Episode We Cover
What seller financing is and where to find sellers who’ll do it
The follow-up question that gets a hesitant seller thinking
Why a higher purchase price can still be the better deal
How to negotiate the rate, down payment, and balloon payment of your seller-financed loan
What happens if you miss a payment or the seller wants out
Why you need an attorney (not an AI template) to make it official
And So Much More!
Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-795.
Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com.
Learn more about your ad choices. Visit megaphone.fm/adchoices - Have you ever seen a “tax hack” online and wondered if it’s actually legal? Putting your logo on your car, renting your home to your business, or moving everything into a trust: a lot of what goes viral is only half true. The other half can draw the IRS’s attention. Here’s how to tell the difference, from people who do this for a living.
Welcome back to the Real Estate Rookie podcast! Live from BPCON 2026 in Orlando, Ashley and Tony sit down with Amanda Han and Matt MacFarland, CPAs and tax strategists at Keystone CPA. They’re also the authors of The Book on Tax Strategies for the Savvy Real Estate Investor. Together they explain the difference between filing your taxes and actually planning them, and which popular real estate tax myths don’t hold up under scrutiny.
You’ll learn how to rent your house to your business (without paying taxes), and why you don’t need an LLC to claim real estate tax benefits. Plus, how the short-term rental loophole creates write-offs for W-2 earners (and where people push it too far), and how it compares to real estate professional tax status. Amanda and Matt even share the one question to ask when vetting a CPA, so you find someone who actually understands rental property investing.
Before you take tax advice from a 30-second TikTok, listen to this episode first, so you can get the tax benefits without the audit!
In This Episode We Cover
The difference between tax filing and tax strategy (one actually saves you money)
Viral “write-off” myths that don’t hold up (logos, cars, and more)
How to document the Augusta Rule (rent out your home to your business) so it stands up in an audit
Why you don’t need an LLC to get real estate tax benefits
How the short-term rental loophole works, and where people take it too far
The one question to ask before hiring a CPA
And So Much More!
Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-794.
Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com.
Learn more about your ad choices. Visit megaphone.fm/adchoices - What if your first (or next) rental didn’t depend on your W-2, your free time, or cash sitting in the bank? Today we’re covering how to qualify for more deals, fit investing around a busy schedule, and fund your repairs without putting your next deal at risk!
Welcome back to another Rookie Reply! First up, we’re breaking down DSCR loans, which let the property’s rent do the qualifying, plus the fine print to check before you sign. Next, a rookie wants to know how to get started with real estate while working 45 to 65 hours a week! We’ll show you how to take those first steps, with help from automation tools and turnkey rentals. Finally, we’re exploring six smart ways to fund repairs after closing!
Not enough income, time, or cash: these are the reasons most rookies never get started. The truth is, there’s a solution for each one, and today’s episode will help you tackle all three!
Looking to invest? Need answers? Ask your question here!
In This Episode We Cover
How to buy rentals with a DSCR loan (even without W-2 income)
How to spot hidden lender fees before you sign
The best real estate strategies for investors with full-time jobs and very busy schedules
How AI and automation can handle guest messages for you
Six ways to fund repairs after you’ve already closed
And So Much More!
Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-793.
Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com.
Learn more about your ad choices. Visit megaphone.fm/adchoices - Is flipping houses still worth it when the market slows down? The easy appreciation days may be over, but investors who underwrite their deals with discipline are still finding ways to win. And today, we’ll explore how you can too!
Welcome back to the Real Estate Rookie podcast! We’re coming to you live from BPCon in Orlando with James Dainard, who has spent 20 years flipping houses and renovating properties in Seattle. James shares how today’s flat market compares to flipping in the years after 2008’s financial crisis, plus the simple shifts that help him protect his profits. By the end, you’ll know how to spot safer deals and plan for surprises so one tough project doesn’t set you back.
James explains why he’s asking for more margin, not less, and the underwriting rules that cushion against longer hold times and price cuts. You’ll learn why homes with multiple exits are the smartest buys for rookie investors right now, and what to look for in a property before adding a detached ADU. Tony also puts his two-year flip on the table, and James walks through whether to sell it, keep it as a rental, or rework the deal with his private money lenders.
Every market shift creates new opportunities for investors who stay disciplined. Tune in, take notes, and get ready to tackle your next flip with confidence!
In This Episode We Cover
Why today’s flipping market feels like the years after 2008
The underwriting rules that protect your profit when prices dip
How to find homes with multiple exits for a safer flip
Using absorption rates to find where buyers are actually buying
Why some flips are worth keeping as rentals (with a future DADU)
What to do when a flip won’t sell, and how to rework a deal with your lenders
And So Much More!
Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-792.
Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com.
Learn more about your ad choices. Visit megaphone.fm/adchoices
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New to real estate investing and not sure where to start? Ashley Kehr and Tony J. Robinson break down the basics with real-world deal analysis, investor interviews and listener Q&A.
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