* Are RealLife boardwalk hotels really so expensive that staying in them for one night can bankrupt a person?
** If you book the entire hotel for yourself, just as you appear to be doing in Monopoly, then likely yes.
*** Can't other people stay in the same hotel at the same time? It'd be fairly rare, of course, but it's unlikely that you'd never see it happen over the course of a game.
* In relation to the above, would that mean that landing on any owned property forces you to stay there and pay for all the rooms, whether anyone lives in them or not? And how do you make one pay the rent for a street?
** Though given that you are travelling around the area in an old boot, a top hat or a steam iron, it's hard to get upset at this minor deviation from authenticity.
** You can't sleep on the street, that's vagrancy, but the house owners won't let you rent out just one house or room, that's Monopoly.
** For that matter, where are you sleeping when you land on the Luxury\Income Tax spaces? Let alone that you have to go exactly as far as you can (dictated by the dice) instead of deciding to stop early for the "day" to avoid having to stop on a rival's property. Even by game standards, it's pretty abstract.
*** Presumably you fell asleep while in the queue at the tax office.
*** It represents business a opportunity for that location. Your Icon is the industry you represent and when you land on a space you want to move your business in, but due to Monopolies by an owner, they force you to sell out, and as the value of property rises due to development, the amount you need to spend to try to muscle in raises as well. Landing on utilities affects everyone in the area since the power producton and water are shared by all the locations, and are needed for your business infrastructure and can be gouged if someone else holds the monopoly. Also you need real-roads to move your goods efficiently (for the time period) so people that control the rail-roads also kick you in the nuts.
* Is there an in-universe justification for why a third consecutive roll of doubles lands you in jail? Like, I can see the "Go to Jail" as sort of like a restricted area where you can pass through, but don't you dare stop. But this doubles thing... I realize it's to put a hard limit on the length of a person's turn in rolls, just... it'd be interesting to see if there's a reasoning beyond that.
** I don't know if it's official, but my family always assumed it means you're speeding.
** Perhaps the in-universe reason for getting to roll again after rolling doubles is something illegal, and doing it too often in a short span got you caught.