Winning: The Real Life Game of Monopoly

Primarily because no one wanted these low-end properties and all I saw was an inexpensive way for a chance to build my portfolio. 
real estate investing pensacola fl


Growing up, one of the board games I played as a child was Monopoly. As we navigate deeper into our Pensacola real estate investing, I’m reminded of those days around the dining room table and think how similar the Monopoly game is to real life investing.

Due to its luxurious nature, I always wanted Boardwalk & Park Place. I knew having a hotel on either of these properties would surely increase my bank roll from any visitor. Here in Pensacola, I correlate that to the high-rise condo on the beach or historic home in East Hill.

real estate investing pensacola fl
Only a lucky roll would push you through my corner rent free!


I also couldn’t stay away from Mediterranean & Baltic Avenues. Primarily because no one wanted these low-end properties, but also because I thought this was an inexpensive way for a chance to build my bank from frequent visitors (plenty of places in west Pensacola fit this model).

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Needless to say, I hardly won the game unless others just wanted to quit due to boredom 🙂  In the game of real life investing, I hardly see where this is the case. My strategy for the childhood game was a slow and steady approach that required a lot of luck. This strategy didn’t produce a lot of winning and comparing to investing today, I realize I learned several valuable lessons playing the game. Maybe its time to break it out again! As I thought about this correlation more, I turned once again to good ol’ Google magic. I stumbled upon a site that really geeks out over the strategy of winning @ the monopoly game. Using our current strategy for buy & hold as a comparative to the game of monopoly, I can see where we are winning @ the game of real estate investing. It is not about the luxurious condo on Pensacola Beach, nor is it about the slums in West Pensacola (done correctly, both of these have their upsides). But the best ROI, winning formula lies in the middle (reference heat map below) of three houses on St. James, Tennessee, and New York and three houses on Kentucky, Indiana, & Illinois. For most of our current positions we’re in that sweet spot. Our others, we’re not too far from it. We buy & hold strictly sticking to several criteria using conservative #s. Using these criteria and with planned exit strategy’s already in place, we’re winning.

Screen Shot 2018-02-05 at 4.00.05 PM

Thanks to the creators of for putting their site together and bringing back some fond childhood memories. The below screenshot is from their site, showing a heat map of the best investment and ROI for the monopoly game.

real estate investing pensacola fl


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Author: W2 Capitalist

I have built this community to connect motivated and ambitious W2 employees who have a successful and fulfilling job but want to build wealth for their family through real estate investing. What makes me the expert? Depends. I’m not the expert to everyone, but I am the expert if you’re behind me on this journey. I’ve been climbing the corporate ladder since 2001 and started actively investing in real estate in 2014. I currently hold a portfolio of 323 units, including single family residences, small multi-family residences and apartment syndications. Since my wife and I started investing, we have grown our net worth 10x and increased our annual income by 60% with these rental properties.

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