Happy Saturday, Housing Heroes,

A wealthy investor once told me:

At first, it sounded too simple to be powerful. But over time, both the data and my own experience have proven him right.

Take the condo I used to live in. I sold it for about $235,000. Today, it’s worth over $535,000. That stings.

Just recently, my wife and I started talking about whether we should sell our current house so we could buy into a neighborhood closer to my son’s school. On paper, it would let us buy something bigger and “nicer.” But we’ve also promised each other we’d never sell this house.

It turns out I’m not alone. According to a 2023 Zillow study, 84% of sellers regret selling, especially in high-demand markets where prices and rents often rise much faster than expected. Once you’re out, it’s hard to get back in.

The First Five Years Are the Hardest

A property manager I know calls it “the five years of pain.”

Why?

• In the early years, your mortgage is mostly interest.
• Expenses feel constant.
• Cash flow looks thin.

But as the loan amortizes, more principal gets paid down. Rents rise. Appreciation compounds.

Sometimes I even run the numbers (with our rent vs. sell calculator) just to remind myself how powerful the long-term payoff is.

Why I Still Won’t Sell

For me, the conviction comes down to three things:

1. I love this house. It’s in a great neighborhood, and I know demand will only grow.
2. It’s a fallback. Worst case scenario? I or my kid can always move back in.
3. It’s simple wealth-building. Even if it “underperforms” against the stock market, real estate still gives me appreciation, amortization, tax savings, and cash flow. It’s an inflation hedge and a diversification play.

And honestly? I think it’ll just be cool one day to tell my son:
“Yeah, we still own that house. It’s part of the family story.”

Reason vs. Purpose

A reason is logical.
A purpose is emotional.

Some rent out a property because:

• Market Conditions: “It’s not a good time to sell.”
• Future Plans: “I might move back in.”
• Experimentation: “I want to see if it works financially.”

Others hold on because:

• Legacy: “I want my kids to inherit something meaningful.”
• Security: “It’s a fallback home if life changes.”
• Passion: “I just love this house.”

A reason will get you started.
A purpose will get you through the storm.

Why This Works Especially Well in California

The California Association of Realtors reports that the median home price has risen from about $421,000 in 2012 to nearly $867,000 in 2025 - more than doubling in just over a decade.

Pair that with strong rental demand and tax advantages, and holding property here becomes a powerful wealth building tool.

How This Strategy Pays Off

Follow that investor’s rule just three times and, in 20–30 years, you could have:

• 2–3 Prime California Rentals – At least one fully paid off, producing steady income.
• Seven-Figure Equity – Even at modest appreciation.
• Built-In Tax Breaks – Depreciation, mortgage interest, and property tax savings.

It’s not flashy.
It’s not overnight.
But it’s the kind of quiet, disciplined strategy that turns one home into a million-dollar legacy.

Why People Quit Early

As Nietzsche put it:

When your “why” is weak, the first challenge an unexpected repair, a tough tenant, or a dip in the market pushes you to sell.

When your “why” is strong, those are just bumps in the road. You see the big picture, and you stay the course.

So now I’m curious…​
Would you hang on to a property and ride out the tough years, or cash in and move on?

Hit reply - I’d love to hear your perspective (and your war stories).

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Our Client's Journey: Episode 1 | Investor Gordon Moss [Never Sell a Home you Live In]

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Steve Welty CEO @ Good Life Property Management DRE #01744610 ​​​​

5252 Balboa Ave #704, San Diego, California 92117
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