496 | “Sell Or Hold?” High Maintenance Rental Property Decisions w/ Michael Santorios Artwork

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Not Your Average Investor Show

496 | “Sell Or Hold?” High Maintenance Rental Property Decisions w/ Michael Santorios

April 20, 2026 • Gregg Cohen / Pablo Gonzalez / Michael Santorios • Season 2 • Episode 496

0:00 | 1:12:12

If a property keeps showing higher maintenance costs, is it still the best place to keep your capital?

This week on the Not Your Average Investor Show, Gregg Cohen and Pablo Gonzalez welcome back Michael Santorios to explore how to think through operational intensity, property performance, and whether a move like a 1031 exchange into newer construction may make sense.

You’ll Learn:
🔁 The 1031 question: What investors should think through before exchanging into newer construction.
📊 Looking beyond surface frustration: How experienced investors evaluate property performance through a bigger portfolio lens.
🏠 Business-minded property decisions: Why costs like tenant upgrades or repairs sometimes need to be weighed against turnover and long-term value.
📈 Portfolio stage matters: How your strategy changes when you move from simply buying properties to optimizing the ones you already own.

This is a helpful episode for investors who want to make more thoughtful portfolio decisions with clarity and confidence.

Listen NOW!

Chapters:

00:00 Sell or Hold Big Questions
01:28 Meet the Hosts and Guest
02:13 Breaking Rent Payout Milestone
03:47 Michael Portfolio Snapshot
05:31 Pacman Profit Centers Explained
07:22 Rebalancing and 1031 Idea
11:00 Maintenance Emotion vs Math
18:03 Greg Numbers Based Reality Check
23:08 Long Term Investing Mindset
28:47 Portfolio Cashflow Scorecard
31:26 Sky Drive Case Study Setup
32:28 Pro Forma vs Actual Returns
35:00 Market Value and ROI Reports
38:12 Tax Savings Explained
38:50 Appreciation And Rent Growth
41:25 Maintenance Surprise Breakdown
45:20 Paying For Big Repairs
47:43 Sell Or Hold Framework
50:51 Cap Rate Comparison
55:04 True Cost Of Selling
01:01:23 Decision To Keep Property
01:04:11 Rapid Fire Q&A Wrap
01:09:27 Final Takeaways And Thanks

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