How to Pick Which Properties to Sell

We’re selling off rental properties. Nope, that’s not clickbait; we’re actually getting rid of cash-flowing rental properties from our real estate portfolios.

But why? And why now?

Is there a market crash we fear is coming? Do we think this is the peak of real estate? Have we finally decided to listen to the social media doomers who keep telling us it’s another 2008? Not quite. Instead, our reasoning behind selling might make a lot more sense than you think. In fact, after you listen to this episode, you might decide to sell some rentals. 

So, what are we doing with the money? Are we going to sit on cash, pay off properties, or retire early? Both Dave and Henry have different reasons for selling, but both agree there’s one thing you should do (at least twice a year) to see whether you should sell properties in your portfolio. 

Thought you were supposed to “hold forever,” as many of the traditional real estate investors have told you? We have proof that selling can often make you much wealthier than holding—here’s how.

In This Episode We Cover

Why we’re selling parts of our rental property portfolios in 2026 

Signs you should sell a rental instead of holding, renovating, or paying it off 

What we’re going to do with the money from our property sales 

Is the market too risky to hold real estate right now? (We may buy even more)

The one thing every investor should do (at least) twice a year to make the highest returns

Buying from landlords? Great deal funnel or overpriced properties?

And So Much More!

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