The small green monopoly houses could be the Kingdom Halls that get put up with quick builds.
The larger red hotels would be the Assembly Halls that get built.
Of course, they would all be 'owned' by the bank...er... watchtower society.
The currently defined 'Jail' and get out of jail scenario would need to be redefined as well. Jail would be redefined to be an assembly. You would go directly to the assembly, foregoing all else. Work, school, etc. Once at the assembly, you would need to throw 'doubles' with the dice, or else stay another round/day. If you stay, you would also need to pay $50.00 err... 'contribute' $50.00 to the assembly. If you never throw doubles, you just stay at the assembly, until your pocketbook is depleted. There is no 'get out of jail' - er... 'asembly' card.
The 'new light' and 'old light' could be something like the amount that you receive when you pass 'go'. Initially it would start out as $200, but you might get a 'chance' card, and it would get redefined by new light to only $150. So, when you pass go, you get $200... no, that's old light. New light says that you only get $150. Since this is not written down anywhere, ultimately, it would cause all sorts of confusion later in the game - especially after getting redefined several times with 'new light' cards.
There also need to be several cards in the deck that predict the end of this system... 1874... 1914... 1975... 1990... any second now. These would get pulled and armageddon would be prophesied as happening that year. The player that pulls the card would be required to ask the player to his left what year armageddon is happening. If his answer does not match that on the card, he is told that his answer is 'old light', and he has to pay $50.00. The date on the card is read aloud, considered as 'new light', and the game continues.
There's a lot that could be redefined to JW-ize the game.
Perhaps monopoly is not the correct game to use. I think that it needs to be a game that has a 'start' and a 'finish'. The goal is to reach finish... only... the cards and dice rolls, etc. do not allow one to ever reach the finish. One might get real close... then get 'new light', and the finish is moved 20 spaces ahead.