10 “Hidden” Signs of a High-Upside Rental Property (Buy These in 2026)

August 12, 2026

AI Summary

5 min read

In 2015 through 2022, real estate deals were obvious. You could buy something and it would cash flow immediately, or you could do a BRRRR and pull all your money out. That era is over. Dave Meyer, Chief Investment Officer at BiggerPockets, calls the current market the "upside era." The central shift is that you now have to buy a deal that is good today—it breaks even or cash flows modestly—and then target two or three hidden "upsides" that could turn it into a great deal over the next three months to three years. The goal is not to find a perfect property with every advantage, but to buy a solid asset that gives you options.

The Core Framework: Good Today, Great Tomorrow

The fundamental rule is that the deal must work as a long-term rental on day one (or after stabilization). If you need every upside to play out perfectly for the numbers to make sense, you are speculating, not investing. The upsides are optional tools that you can deploy opportunistically—when a tenant moves out, when market conditions shift, or when you have the time and capital. Meyer's original list had ten upsides, but he now believes some have changed in importance. The most reliable ones today are those you can force through your own actions, not those you have to wait for the market to give you.

Value Add: The Most Reliable Upside

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What you'll learn

1 (00:00) **The Upside Era Defined** - Dave introduces the concept of buying properties with hidden upside (rent growth, value-add, path of progress) to turn good deals into great ones.
2 (03:07) **The 10 Upsides Framework** - Dave lists his original 10 upsides for rental properties, emphasizing you only need 2-3 per deal.
3 (04:57) **Rent Growth: Least Bullish Upside** - Dave explains why pure rent growth is now the least reliable upside and how to evaluate it.
4 (07:33) **Value-Add: Tiered Opportunities** - Dave and Henry break down short-term vs. long-term value-add strategies.
5 (15:28) **Owner-Occupied as an Upside** - Dave explains why house hacking and live-in flips are perfect for the upside era.
6 (17:33) **Rent by the Room: A Management Tool** - Dave frames rent-by-room as an optional management strategy, not a standalone investment approach.
7 (24:58) **The Free Land Upside (Henry's Addition)** - Henry introduces his 11th upside: buying properties on large lots and splitting off excess land for pure profit.

+ Full timestamped outline available in the app

Guests on this episode

Dave Meyer Henry Washington

Show Notes

The “regular” rental property you’re thinking of buying? It may not look like anything special here in 2026, but it could be worth tens or even hundreds of thousands of dollars more down the road—IF it has any of the high-upside qualities we’re about to show you.

For the last 18 months, I’ve said that this is real estate investing’s era of “upside.” The “easy” real estate deals you could buy in 2015-2022 are long gone, and what we’re left with are a lot of seemingly unspectacular properties—but ones with hidden upside that is just waiting to be unearthed.

A property with one of these qualities is unlikely to make you rich on its own. You’ve still got to focus on buying high-quality assets at good prices today. But if your property has two, three, or more of these “upside” opportunities, its value could skyrocket five, 10, or 20 years from now.

This isn't just about market-driven appreciation. These are 10 distinct advantages that aren’t on most buyers’ minds when they’re looking for a simple deal that will cash flow, but thinking about them now could pay massive dividends in the future.

In This Episode We Cover

The 10 upside plays that can turn a “good” property into an all-time deal

Value-add opportunities that can add hundreds of thousands of dollars in equity

The huge advantages of owner-occupied strategies (not just better financing)

How to identify properties that have zoning upside or lie in the path of progress

Henry’s “free” land upside play that most real estate investors take for granted

And So Much More!

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