Sizing risk for smaller operators

James advises smaller investors to reduce risk, stick to known project types, and rely on proven contractors.

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Episode notes

This could be the best real estate “buy” of 2026. While mortgage rates are climbing back up and everyone is waiting out the housing market—again—one man is going all in: James Dainard.

If you’ve listened to On the Market for a while, you know James is never not buying—but what he’s buying changes by the week, or even by the day. Last year, James got burned (a bit) on house flipping and new development, but reassessed his almost unbeatable investing framework and is now saying there’s one particular asset class he’s hungry to acquire—and it’s on serious discount.

So today, we’re picking the brain of the man with 1,000+ rental units who’s flipped thousands of homes and knows the market better than any economist, since he’s on the ground buying and selling every single day.

James shares the “best buy” of 2026, the one thing you must account for if you’re flipping or doing any renovation project, the single best rental for small investors to start with (and how to find them on-market at discount), and the one high-return deal he’d do as a new real estate investor.

This is what’s working in real estate right now in 2026.

In This Episode We Cover

The overlooked (and underpriced) properties James is heavily targeting in 2026

How to find on-market, discounted rentals perfect for small investors

The “buyer psychology” changes in the market that flippers must be aware of

One high-return real estate deal new investors should heavily consider in 2026

One cost to add to every renovation project to ensure you stay on budget

And So Much More!

Links from the Show

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