What Monopoly and the Beatles Can Teach You About Buying Your First Investment Property

Without overthinking it… if you were sitting down to play a game of Monopoly, which two properties would you most want to own?

There’s a decent chance Park Place and Boardwalk crossed your mind.

They’re expensive. They feel prestigious. They’re kind of the Monopoly version of making it. And if you’re being investment-minded, they probably seem like the smartest things to own if your goal is cashing in when other players land on your properties.

If those were your picks, apparently you’d be in good company.

Journalist Art Schreiber, who spent time traveling with and interviewing The Beatles over the years, once shared that the group enjoyed playing Monopoly together. According to this article, Schreiber said John Lennon didn’t actually seem all that concerned with winning… he just wanted Park Place and Boardwalk.

Honestly, that’s really not all that surprising. Plenty of people set their sights on those two properties. The more intriguing detail from the story is that George Harrison set his sights on B&O Railroad. And what’s even more intriguing is that he never would never explain why.

Which leaves us to speculate….

Is B&O Railroad Better Than Boardwalk?

Park Place and Boardwalk can certainly create massive paydays.

But first, you have to be lucky enough to land on them before somebody else does and have enough Monopoly money to buy them. Then you have to spend even more money building houses and hotels… and after all of that, you still have to wait for the roll of the dice to send other players your way.

According to this article, Boardwalk ranks #16 when it comes to the spaces players land on most frequently. On the other hand, B&O Railroad is the #2 spot! And Reading Railroad comes in at #4.

The article even suggests that buying railroads early in the game is a great strategy because they cost nothing to build up, and they can provide a constant income stream that helps fund everything else you do later in the game.

So maybe George Harrison was onto something and didn’t want to share his trade secrets. It might be worth trying the railroad strategy the next time you find yourself playing Monopoly.

But when it comes to investing in actual real estate, your first investment property isn’t something you want to choose based on a roll of the dice. After all, you’re not playing with Monopoly money in real life.

Know Your Options Before You Put Real Money on the Board

In Monopoly, everybody is playing the same game with the same rules, the same starting cash, and the same fixed array of properties to buy.

There are a lot more variables and options in real life!

Some people invest in single-family homes. Others prefer condos, multi-family properties, vacation rentals, commercial properties, or land. Some investors are looking for monthly cash flow. Others care more about appreciation over time. Some want something lower maintenance while others are comfortable taking on more work in exchange for more upside.

And that’s before you even start factoring in budget, financing options, local market conditions, risk tolerance, and how involved you actually want to be.

Just like Monopoly, there isn’t one universally “best” property. Park Place isn’t automatically right. B&O Railroad isn’t automatically right.

The goal isn’t finding the property that sounds the most impressive or buying the one that seems like a great deal at first glance. The goal is finding the investment that makes sense for your goals and understanding the tradeoffs that come with it.

That’s one of the biggest reasons it can help to talk with a knowledgeable real estate agent before making your first investment purchase. They can help you explore options you may not have considered, look at local trends and numbers, and think through different approaches before you put real money on the board.

The Takeaway:
John Lennon reportedly loved owning Park Place and Boardwalk when playing Monopoly, while George Harrison quietly preferred B&O Railroad. Whether George had discovered some secret strategy or simply liked the railroad, it’s a good reminder that there’s often more than one way to approach investing.
Real estate investing in real life works much the same way. There are many different ways to invest and many different types of properties to consider.
If buying your first investment property is something you’ve been thinking about, it may be worth talking with a knowledgeable real estate agent before making your move. They can help you understand your options, evaluate opportunities, and build a strategy based upon your goals.