I would update the theme to that of the gentrification of neighborhoods. Players could purchase vacant store fronts as cafe, bars, retail ventures. Properties closer to public transportation would have a higher purchase price than those further removed. Buildings could be bought,and remodeled as either rental units or for purchase as single home structures. Update the car to either an SUV or a hybrid vehicle, keep the hat, the thimble could be replaced by a laptop, etc. Add a tree as a playable piece.
Get rid of the "Get out of jail free" card.

Go Straight to Jail card but have it apply to the following: rental slum lord, building code violation, health code violation, too many tenants in a building, etc.

jeffrey