In the game this is exemplified by forcing you to progress through life on a preset course and force you to pay rents to the incumbents that you come across on that narrow path.
The dice roll of course represents that life is unpredictable. But I struggle to find the real world analogy where I go bankrupt because I randomly end up in a hotel in Park Avenue.
Never mind the fact that you are forced to move every day from a location you likely can easily afford to a new location not knowing whether you can afford it or not. How can you plan for the future when you move from $200 rent to $2000 rent in a single day with no new income?
What strange shenanigans is going on that compels me to move so much? Especially moving into hotels when I previously lived in a house.
For that matter, if a property doesn't have a house nor hotel what am I paying rent for? The street?
Also, why can't I build a house on my property unless I own the two or three properties in the same area?
I also fail to see how one is supposed to learn anything about economics from the game other than just the basics that takes five minutes to explain.
Modern economics? No. Land-title-era economics, where owning land meant you had autocratic control over it and could kick people out of it? Yes. To translate to modern economics, you have to change the names of things a bit.
Picture each set of colored properties as a separate country. You are an entrepreneur, so when you land in a country, you implicitly try to start a business there. The "base rent" for that country is the cost of doing business--corporate tax rate et al.
Each square within a country is an industry. As you build "houses" and then "hotels", you take over that industry. (Houses and hotels themselves make sense as markers if the industry you're taking over is real-estate; otherwise, interpret them as the symbolic equivalents for their own industry. For a manufacturing industry, this would be exclusivity deals with parts of the supply chain. Etc.)
When you've got a full set of houses on a square, you have a monopoly in that industry. This isn't as useful, though, as having bargaining/lobbying power from multiple industries that operate in the same country--having houses on all the squares. When you do that, you can convince the government to give you their contracts--to enforce the mega-monopolies for you, like in telecommunications or defense. These claims are represented by the hotels.
When you land on a square, and someone else has a monopoly there already? Your implicit entrepreneurial bid will be quite a bit more costly. But, of course, your customers expect you to expand into new territories, even if someone else controls them, so expand you must.
(I'm not sure what the railroads and such then represent, though. There aren't that many global utilities that actually give people power when they control them; the shipping-container era kind of fixed that. The internet backbone might seem to be a contender, but it doesn't really make that much money for the people who control it.)
The dice roll of course represents that life is unpredictable. But I struggle to find the real world analogy where I go bankrupt because I randomly end up in a hotel in Park Avenue.