Itadaki Street is simply explained as Enix’s take on Monopoly. When Square and Enix merged they threw Final Fantasy and Dragon Quest characters into Itadaki Street resulting in the first Cloud meets blue slime crossover. Jenni has a fantastic write up on the handheld entries in case you’re curious about those.
The latest Itadaki Street game stuck with the Final Fantasy trend and added Lighting to the roster. That’s her made “chibi” above. Just like Cloud and Squall, Lightning is too cool to smile.