DiGiCharat's Game of Life (1997)

Loosely based off Milton Bradley's Game of Life but with more choices to be made throughout the game. This version is based off the anime DiGiCharat. DiGiCharat being the cute catgirl on the cover that is also the mascot character for the "Gamers" line of stores in Japan and their parent company Broccoli. It's still an extremely 'light' game. You can change occupations many times throughout the game, and collect items that are worth money at the end of the game (or you can have items worth negative money that you want to try to get rid of). There's good-natured "Fight" squares and the like as well.