On The Market

Vacation rental markets were some of the biggest winners of the housing boom several years ago. But where are those real estate markets today?



New data suggests that many of the operators who chased cash flow in the Airbnb gold rush are now looking to cut their short-term rentals loose. As it turns out, running a profitable Airbnb is much harder than it looks. So, does that make this the perfect time to buy?



Our resident short-term rental expert, Garrett Brown, joins the show to break down exactly what’s happening and why it could be worth making a few “disrespectful” offers on these types of properties in 2026.



Sellers are highly motivated, and more properties are hitting the market, but investors must be able to distinguish the “good” rental properties from the homes that should never have been vacation rentals in the first place. We’ll get into market analysis, the amenities that actually drive bookings, and why the next wave of successful short-term rental investors will win with hospitality—not hype.

In This Episode We Cover

The exact type of operator being squeezed out of vacation rental markets

The two types of short-term rentals that are still wildly profitable in 2026

Why there are so many motivated sellers in the short-term rental space right now

Garrett’s favorite short-term rental markets to target in 2026

The number one thing you must do when entering a new Airbnb market

And So Much More!

Links from the Show

Join the Future of Real Estate Investing with Fundrise

Join BiggerPockets for FREE

Join us at the BiggerPockets Conference October 2-4 in Orlando. Buy tickets

Sign Up for the Investor Brief Newsletter

Find an Investor-Friendly Agent in Your Area

Investing in Short-Term Rentals: A Beginner’s Guide & How to Get Started

Garrett's BiggerPockets Profile

Dave's BiggerPockets Profile

Watch Garrett on BiggerStays!

Parcl: Trouble in Paradise: America’s Vacation-Home Sellers Are the Most Motivated in Housing

AirDNA

BNBCalc

Buy the Book, Smarter Short-Term Rentals

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If you’re investing in real estate, you’re probably asking, “How much can this property make me?” But in 2026, it’s the opposite question that actually builds your wealth: “How much can this property cost me?” You’re seeing discounted deals on the listing sites; realtors and brokers may even be sending you off-market listings that look like steals. How do you know whether you should pass on them or not?

James and Kathy are on today to talk about which deals they’re passing on, and the underrated land play that’s making serious returns and requires no building to profit. Kathy almost closed on the perfect medium-sized multifamily deal in a great location, newly built, and with a pool of tenants nearby. But one seemingly small problem made her walk away—if she hadn't, she could have lost tens or hundreds of thousands. Would you be able to spot the mistake?

But a land investment is making both Kathy and James very excited. You don’t need to build anything on the land, you don’t need to rent the land, you don’t even need to get utilities on the land. This strategy, especially the way Kathy is using it, could profit big time if interest rates drop even slightly or demand picks up. The question is, how do you get into it without the risk of speculation?

In This Episode We Cover

The real estate deals we’re actively passing on in 2026 (they aren’t worth the headache)

A land investment play that could come with big profits if done the right way

One small problem that made Kathy walk away from a multifamily deal with exceptional numbers

Are the 30%-off multifamily deals finally worth the money, or are sellers asking for too much?

Kathy’s exact buy box for what she will and won’t invest in this year

And So Much More!

Links from the Show

Join the Future of Real Estate Investing with Fundrise

Join BiggerPockets for FREE

Join us at the BiggerPockets Conference October 2-4 in Orlando. Buy tickets

Sign Up for the Investor Brief Newsletter

Find Investor-Friendly Lenders

BiggerPockets Real Estate 1039 - The Hidden Opportunity of Property “Rezoning” Making This Investor Wealthy

James' BiggerPockets Profile

Kathy's BiggerPockets Profile

Run the Numbers Before You Buy with Real Estate by the Numbers

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Nearly 50% of mortgages in the U.S. flow through Fannie Mae or Freddie Mac—but a push from the Trump Administration could sell shares of these government enterprises and put them in the hands of the public. The side effects could be significant to those getting or refinancing a mortgage—from interest rates to regulations.

Fannie Mae and Freddie Mac alone take up about half of the mortgage market. The reason you can get a 30-year loan, a lower interest rate, and do it all with standardized regulations is largely thanks to Fannie Mae and Freddie Mac. So, if these enterprises are sold on the private market with Freddie Mac and Fannie Mae IPO-ing, would it put so much privatized pressure on the mortgage market that it could begin to break?

Today, we’re getting into the major consequences from a sale of Fannie and Freddie—currently owned almost entirely by the government. With a $250B payday sitting in limbo, the government could be pushed to sell off the enterprises that enabled average Americans to buy houses. The question is, should it even happen?

In This Episode We Cover

The Fannie Mae and Freddie Mac IPO possibilities and the side effects it would have on mortgage rates and regulations

Why the government took over Fannie and Freddie and whether re-privatizing them will encourage these enterprises to do anything to profit

The massive payday that could come out of a selective sale of Fannie and Freddie

Pros and cons of a sale going through and whether Dave thinks it’s a smart idea

And So Much More!

Links from the Show

Join the Future of Real Estate Investing with Fundrise

Join BiggerPockets for FREE

Join us at the BiggerPockets Conference October 2-4 in Orlando. Buy tickets

Sign Up for the Investor Brief Newsletter

Find Investor-Friendly Lenders

How Privatizing Fannie Mae and Freddie Mac Could Have Seismic Impacts On Real Estate

Dave's BiggerPockets Profile

Grab Dave’s Book, Real Estate by the Numbers

Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and https://www.biggerpockets.com/blog/on-the-market-447.

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This isn’t a “good” housing market for anyone. Affordability remains a major barrier to homeownership. Sellers aren’t getting what they want for their homes. Now, builders are signaling that the current housing shortage could get even worse. It’s bad news for aspiring homeowners, but could it finally put a floor on this housing market correction?



This week’s headlines highlight how affordability challenges are reaching every corner of the housing market—not just for buyers. A perfect storm of high interest rates, stagnant home prices, and rising material and labor costs is putting builders under pressure, too. As a result, housing starts and single-family home completions have reached their lowest levels since 2020. But could this slowdown ultimately limit how far home prices can fall?



At the same time, there are other factors keeping homes off the market—like a potential capital gains tax problem discouraging many baby boomers from listing their homes for sale. Meanwhile, house flippers are worried about another tax coming down the pipeline that could eat into even more of their profits. Everyone’s feeling the squeeze, but could these pressures causing the market to bend be the same forces that prevent it from breaking?

In This Episode We Cover

Why the single-family market correction may have just found its floor

Why many homebuilders are building less amid a national housing shortage

Whether we should raise the capital gains tax exclusion for homeowners

A new tax that could cost house flippers even more of their margins

Three issues that are potentially contributing to a stagnant housing market

And So Much More!

Links from the Show

Join the Future of Real Estate Investing with Fundrise

Join BiggerPockets for FREE

Join us at the BiggerPockets Conference October 2-4 in Orlando. Buy tickets

Sign Up for the Investor Brief Newsletter

Find an Investor-Friendly Agent in Your Area

Flippers Supplied 2x More Starter Homes Than Builders in 2025

Dave's BiggerPockets Profile

Henry's BiggerPockets Profile

James' BiggerPockets Profile

Kathy's BiggerPockets Profile

CRE Daily: US Housing Starts Slow, Giving Apartments Room to Recover

AEI Housing Center: Capital Gains Rules on Home Sales and Senior Homeowner Lock In

The Real Deal: “The math has stopped working”: NYC home flipping drops as state legislators propose new tax

Grab The Book on Tax Strategies for the Savvy Real Estate Investor

Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and https://www.biggerpockets.com/blog/on-the-market-446.

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The average American will not be able to retire. 50% are going into their golden years with less than $500,000—significantly short of what would even be considered a livable retirement amount. Social Security only has so long before payments begin to get cut, and retiring during a stock market crash, or even a correction, can put you at sizable risk of returning to work.

But one asset can help you retire with less, reach retirement (or even early retirement) faster, and do so without putting your future freedom at risk—real estate. Today, Dave is going to prove why so many of his retirement plans sit on rental properties as a stable base, and how Americans can retire with up to 50% less using real estate, as opposed to stocks and bonds.

This flips the entire retirement equation on its head. Now you don’t need to bet on the market, you don’t need to hope and pray Social Security will exist when it’s your turn to collect, and you don’t need to hit some sky-high ($4,000,000+) retirement number just to live a comfortable life.

This is the faster, and arguably safer, formula for retirement in 2026 and beyond.

In This Episode We Cover

How to retire with far less using real estate cash flow (instead of selling stocks)

How much you actually need to retire in the United States (inflation-adjusted)

The real estate retirement framework that gives you better returns, more cash flow, and a simpler path

Why 81% of Americans are at risk of never being able to comfortably, confidently retire

The problem with building a cash flow-focused real estate portfolio too early (it will cost you)

And So Much More!

Links from the Show

Join the Future of Real Estate Investing with Fundrise

Join BiggerPockets for FREE

Join us at the BiggerPockets Conference October 2-4 in Orlando. Buy tickets

Sign Up for the Investor Brief Newsletter

Find an Investor-Friendly Agent in Your Area

How Much Passive Income is Enough to Retire With?

Schroders US Retirement Survey

Dave's BiggerPockets Profile

Grab Dave’s Book, Real Estate by the Numbers

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