TBT: How Do I Know When To Sell My Property?

Passive Real Estate Investing

Real Estate Investing with Marco Santarelli, Investor and Entrepreneur.

Investing, How To, Business:investing, Education, Entrepreneurship, Business

4.7 • 967 Ratings

🗓️ 12 March 2026

⏱️ 19 minutes

🔗️ Recording | iTunes | RSS

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Summary

Click Here for the Show Notes Feeling stuck with a rental property that’s draining your wallet instead of building your wealth? In this episode, Marco answers a listener question from Kelly, who’s been struggling with two Baltimore properties that have produced over $20,000 in losses, constant tenant issues, damages, and even squatters. Marco breaks down the key factors every investor should analyze before deciding whether to hold or sell—like market trends, return on equity, neighborhood quality, property performance, maintenance risks, and personal financial goals. He also explains the “tipping point” where negative cash flow and ongoing stress may signal it’s time to reposition your equity into better-performing assets. If you’re wondering whether a struggling rental is worth keeping—or when to cut your losses—this episode offers practical insights to help you make a smarter, more strategic decision. 🎧 Listen now to learn how to evaluate your properties like a seasoned investor! -------------------------------- Throwback Thursday Episode (The episode originally took place in the year 2024) This episode is part of our Throwback Series and may include references to older content such as web classes, events, promotions, or links that are no longer active or available. While the conversation and insights still hold value, please note that some information may be outdated. -------------------------------- If you missed our last episode, be sure to listen to TBT: The REAL Returns of Real Estate Investing Download your FREE copy of: The Ultimate Guide to Passive Real Estate Investing. See our available Turnkey Cash-Flow Rental Properties. Our team of Investment Counselors has much more inventory available than what you see on our website. Contact us today for more deals.

Transcript

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0:00.0	Welcome to passive real estate investing, the show where busy people like you learn how to build substantial passive income while creating wealth for the long term. And now, here's your host, Marco Santorelli.
0:13.0	Hello, my friends. Welcome back to passive real estate investing, where we dive into the world of real estate investing, among other related topics, to help you with your real estate investing journey.
0:23.5	Today, we're doing something a little different.
0:26.2	We're going to take a trip down memory lane and showcase an important episode from the past on what we call our throwback Thursday episode.
0:34.5	Now, whether you've been with us since the beginning, which goes back to 2015,
0:38.8	or you're tuning in for the first time, this episode is a must listen. We are revisiting one of our
0:45.4	more popular episodes from the past. And believe me, what we discussed back then, whether it's
0:51.0	six months ago or six years ago, is just as relevant today. So sit back,
0:56.5	relax, and let's rewind the clock for this great episode. Enjoy. Today I wanted to grab a question
1:02.6	from the pile of Ask Marco Questions, and I think there's some really good ones that have
1:08.5	been coming in recently, So I appreciate the questions.
1:11.5	I'll try and batch some of them and some of them I'll just take individually.
1:14.8	But Kelly wrote in not long ago and was asking a question about whether or not to sell their property or when to sell their property.
1:25.7	And the question is basically this.
1:29.5	I have two properties in Baltimore and I have been cash flow negative for one year. It's been difficult and nerve-wracking knowing I've
1:34.9	paid over $20,000 in the last year to simply hold these two properties. In the last six months,
1:40.6	it has been especially hard and I've been paying both mortgages at $2,000 a month.
1:45.1	I have had damages, turnover, squatters, you name it. I keep hoping that things will turn
1:50.7	around. I've been trying to learn about return on equity, ROE, but it's not clear to me what
1:56.8	percentage is too low and for how long I should wait. How do I analyze whether to sell my
2:01.6	properties? What is the tipping point in holding versus selling? Thank you so much, Marco.
2:06.4	All right, Kelly. Well, I appreciate the question. It's a great question. I've got obviously
	...

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