Complete a game with $20+
Obtained one of two ways:
Easiest method is to start a long game and answer the quiz with the ‘wealthy’ options. Visit the library every chance to make money. Each visit nets you $2 and depending on the dialogue you can gain more or lose depending on your response.
RNG method you can buy ‘The Gift That Keeps on Giving’ for $0 and potentially get the lottery ticket which you will also nab another achievement for completing the game with $99+