Maya Marston is on a mission. She is absolutely positive (almost) that some heavenly intervention will send the winning lottery numbers her way, she's just not quite sure how. Enter 5 year old Casey, daughter of Maya's new tenant Summer Dey, who has a love of numbers and might just be the answer to Maya's prayers. Maya is sure Casey will come up with the winning numbers so she enlists her sidekick Gladys, a mousy little woman who knows where every 7-eleven store in San Diego is located and Maya's virgin son Robert, who is jobless and has plenty of time to help out. When their adventures and misadventures require the need for travel, Robert enlists his best friend JoJo, a drag queen with a pink Cadillac and a lead foot. Maya has spent the last two months distracted by the quest for the winning numbers and now realizes that she has forgotten to pay the mortgage. Could the mysterious man in black who they have been avoiding be trying to kick them out of their house as Maya believes? How can they keep hiding from him if he has started a romance with Summer Dey? What about the ever handsome Brock Donovan? Will he steal Maya's heart or just her money? Maya has been hoping for Pennies from Heaven but she now realizes they could be Pennies from Hell.