I just realized, I just bloody realized, Moist Von Lipwig’s story arc is a game of Monopoly through the eyes of a conman going through the board and winning all the pieces.
He has the top hat, the dog, the train (which replaces to automotive in newer boards) the friendship of the Seamstress’ Guild (thimble), the walking iron called Gladys, the boot (he’s the incarnation of the Disc God Fedecks who has winged boots) and also the bag of money.* He goes to jail, but eventually gets to pass and go. He’s integral in the rehabilitation of civic buildings (post office, bank, mint, the acquisition of land to build a railway and then adding stations to said railway), the owner of up market private property, and also he invents paper money which everyone sort of thinks of as a bit of a game.
His very name, Moist Von Lipwig, is a pun about wearing a fake lip wig or mustache. Like so:
Lord Vetinari is quite literally using him to play a life size version of Monopoly with the city. And winning.
(Amendment: Adora with hear deadly footwear is also the shoe/boot.)
(* Alternates: Sam Vimes is boots, Gaspode and Beggars Guild is dog, Wheelbarrow is Harry King, Thimble is Seamstress Guild, Battlehsip/canon is Assassins Guild/Nobility, Money Bag is Thieves Guild, leaving Moist as Top Hat and Train. ANKH-MORPORK MONOPOLY, GIVE IT TO ME)
((edited for typos, too busy flailing))!!!!!