It just seems...pointlessly mean.
As you say, there are ways you could re-frame the game to reflect the new economy and how young people live within it
Like renting property until you can buy a house but you still need to loan that house out to Airbnb for
X months per year to pay the mortgage, or buying a car that earns you money as a Lyft driver but costs you money in upkeep, or juggling contract work with tax and health insurance payments, or basically any of the ways that MANY millennials live their lives
Plus options for trade school vs. traditional college vs. no college, and what kind of debt/choices each of those afford to players.
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Or getting to the end of the game and realizing that Google and Amazon were the real monopolies all along