TMP has fallen to Fourth Place! Gold is still in First Place; Stocks rallied to Second Place; Oil holds third (both probably boosted by the ongoing Iran situation). The Bond Market continues to lag — as usual. (Don’t buy bonds… even James Bond.)

The Seven Year Itch

We’re now in the seventh year of The Monopoly Project. And we’ve fallen to fourth place.  After all that work — and yes, managing real estate properties is work — three purely passive investments (Gold, Stocks, and Oil) are ahead of us. Did we waste our time? Should we just sell out and put everything into those three?  No, no, and no.  This is exactly where lots of people quit. Real estate is a long-term play, and the “itch” after several years of active effort is completely normal. You’re not alone in feeling it.

What the Pros Say About Sticking It Out

You’re not the first real estate investor to hit this moment — and the biggest names in the space all emphasize the same thing: persistence wins.

  • Financial Samurai has written extensively about why real estate rewards patience more than almost any other asset. In “Why the Feel-Good Wealth Effect From Real Estate Beats Stocks,” they point out that real estate gains feel more permanent because they take real work, discipline, ongoing maintenance, and long holding periods. Another favorite of mine is “Private Real Estate Investing: Seven Takeaways After Ten Years,” which drives home the core message: “Your goal as a real estate investor is to hold on for as long as possible. The longer you can hold on, the more you will likely make.”
  • Coach Carson (a huge advocate of house hacking and long-term rentals) constantly highlights buy-and-hold strategies. His content on long-term rental investing shows how the slow-and-steady approach — rental income, tax benefits, loan paydown, and appreciation — compounds beautifully over 7–15+ years, even when passive index funds look sexier in the short run.
  • BiggerPockets, the largest real estate investor community, is full of real stories that mirror our situation. Their guide to the Buy & Hold strategy and numerous member success posts (including multiple accounts of investors who went from $0 to seven figures in roughly seven years) prove the same point: the people who push through the middle years are the ones who build lasting wealth.

These sites reinforce what we already know deep down — the investors who quit at year 7 are usually the ones who miss the biggest gains.

Why We’re Not Selling

Real estate isn’t just another asset class. It’s an active one that gives us advantages passive investments simply can’t match:

  • Leverage (we control millions in assets with far less of our own capital)
  • Depreciation write-offs
  • Mortgage paydown by tenants
  • The ability to force appreciation through improvements
  • Inflation-hedging cash flow that stocks and gold don’t provide

We’ve put in the work. Our four properties are paid down, cash-flowing, and positioned for the next decade. This isn’t a sprint — it’s the long game we signed up for.

What Else We’re Doing Besides Managing Real Estate

Plenty! Life isn’t only spreadsheets and tenant calls.  For example, I entered a local chess tournament with my grandson James. It was a lot of fun that didn’t involve screens. We both ended up with three wins and one loss (3–1 records). I came in first in the Intermediate group, while James tied for first in the Beginner group.

Here’s Jim and James with their awards:

Figure 1 Jim and James after sweeping their sections of the local chess tournament — 3 wins, 1 loss each. Real estate isn’t the only game we play!

Figure 2 Jim at work in Game 4 with spectators

GROK Analysis: Verdict on the attack;

“Brilliant and brave by Luke (Black). It created enormous practical problems and would have crushed most players. Jim (White) showed excellent composure under fire, captured everything on g3, and immediately switched to a crushing counterattack on the queenside/center with 26. Nxc7 and the knight maneuvers that followed.

The game swung from “Black is winning” to “White is winning” in just a few moves — classic club chess drama!”

Figure 3 James at work.

The Bottom Line

Here we are in year seven of The Monopoly Project — a little behind on the scoreboard but richer in experience, memories, and a paid-off portfolio that will keep cash-flowing for decades. We’re not selling. We’re doubling down.  What about you? Have you ever hit a “seven year itch” in your investing journey — whether with real estate, stocks, or anything else? Drop a comment below or shoot us a message at TheMonopolyProject.com — we read every one.

Let’s keep building.