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The Ramsey Show Highlights

Short-Term Rental Nightmare (Losing $2,500 A Month)

The Ramsey Show Highlights

Ramsey Network

Investing, Education, Business, Self-improvement

4.5838 Ratings

🗓️ 25 May 2026

⏱️ 10 minutes

🧾️ Download transcript

Summary

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Transcript

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0:00.0

brought to you by the every dollar app start budgeting for free today my wife and i purchased a

0:08.3

short-term rental um in october of 2024 and uh at the advice of a tax strategist that we hired um

0:17.2

and we're bleeding 2 500 to 3 grand a month in this short-term rental.

0:22.7

Okay.

0:24.5

And I own a business.

0:26.4

My wife's a full-time nurse, and we get taxed heavily.

0:30.0

Obviously, the business does.

0:31.1

And that's why I enlisted with a tax strategist to understand, you know, options, you know,

0:36.1

as far as building generational wealth and how to do that.

0:39.1

And that's when we got into the short-term rental. And, you know, we got bonus appreciation, so that was nice. You know, we were able to write off the federal taxes and stuff. But bleeding $2,500 to $3,000 a month is not, doesn't leave very good taste in my mouth. Of course not. You might as well pay that to the government and taxes at that point if you're just going to bleed it.

0:55.3

You're either giving it to well pay that to the government and taxes at that point if you're just going to

0:55.0

bleed it.

0:55.4

Like, I might as well not even do it.

0:56.3

You're either giving it to a lender or to the IRS. Pick your poison. Correct. Correct. So my real main question is, you know, what I'm really, it's hard for me to trust people now because of how, you know, this leaves

1:09.4

how our taste in my mouth. And I just need

1:11.3

really good direction. You know, what do we do with

1:13.4

our money to help

1:14.5

build generational wealth, to find properties that cash flow? What should my next steps be?

1:21.1

What is your business?

1:22.0

We want to do something this year, but I'm nervous. We own a print company. Okay. Where do

1:26.7

the real estate come into play?

1:27.9

Because these are two different goals.

...

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