Gee, we redesigned Monopoly in the 60s in Berkeley, and everyone had a great time. In addition to some money in Free Parking, we would place a lovingly rolled joint. When someone hit free parking, it was light up time, and everyone was a winner! After a couple of times... well we actually would never finish the game, but no one cared.... so much for capitalism in the old days.

With regards to the bailout, it may be important to include a "Last Chance" deck that includes options like government help to, who knows, rolling a die to see if the player's insurance scam of burning down a property works. And to allow for more uses of land that have different effects, and let some of them be detrimental, i.e., setting up a factory gains you a steady income that doesn't demand other players landing, "and" it severely reduced the value of its neighbor properties, unless they are industrial, too, so you can ruin someone's burgeoning loft or hotel district with a big old factory. By making land values the basis of rent, and letting those land values be affected by how the surrounding land is used, could make the game more interactive and cutthroat. And, perhaps, allow for players to invest in one another's ventures, or even "take over" them.