How to Pick Winning Real Estate Deals Without Guessing

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In this episode, I break down how I analyze real estate deals using patterns, historical percentages, and what I call “return on hassle.” I share a story about a 16-unit property I almost bought to retire my mom and how a mentor helped me realize it wouldn’t work—just by looking at the percentages. I go deep into operating expense ratios, debt service thresholds, and how to factor in time and risk. I also touch on contracts, financing contingencies, and why I only move on deals that match my strike zone.

Timestamps:

00:00:00 Intro – why percentages never lie

00:00:50 The 16-unit deal I almost bought to retire my mom

00:02:15 Bringing in a mentor to review the numbers

00:03:28 Learning to read patterns in properties and people

00:04:11 Scarface quote and the power of percentages

00:05:46 Ted Williams and only swinging at your pitch

00:08:13 Applying the strike zone concept to investing

00:09:14 Long-term rental analysis: revenue, OPEX, debt

00:11:45 Utility setups and checking meters on multifamily

00:13:54 Margin of error and padding your projections

00:14:42 Short-term rental rules and the 15% revenue test

00:16:16 Sneaky data hacks: talking to local co-hosts

00:18:29 Evaluating money down vs. ROI on interest savings

00:20:50 Guaranteed returns and the “return on hassle” concept

00:23:00 FHA vs. conventional loan and PMI traps

00:27:54 Why you must revisit the numbers at month 16

00:29:04 Diagnosing why a deal is underperforming

00:31:08 Pattern recognition and IRS fraud flags

00:33:40 What’s included in operating expenses?

00:36:28 Community, status, and why people never downgrade

00:39:53 Appreciation markets vs. cash flow plays

00:41:33 Writing contracts with flexibility: “and/or assign”

00:44:05 Laying out all the skunks as a seller

00:46:02 Contingencies: inspection, appraisal, financing, permits

00:51:04 Buying the LLC to preserve STR permits

00:54:20 DSCR strategy and using interest rate leverage

00:56:05 Only swing at your pitch and know your advantage

00:58:16 Speed, trust, and recognizing patterns in people

01:00:32 Final thoughts and the value of knowing your safety net

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*None of this is meant to be specific investment advice, it's for entertainment purposes only.