Kai and Bernette's recent house-buying spree in South Side Chicago means they're now cash-strapped and can't afford to get their flipping dreams off the ground. Sean agrees to finance their first flip, but even a blueprint for success is no guarantee.

Chantill and Larry's latest project on Chicago's South Side was supposed to be a major moneymaker, but they put their trust in the wrong people and are now in dire straits. Sean steps in with a plan, but it's a white-knuckle ride to the finish complete with a dramatic confrontation that has their buyer running for the hills.

Professional flippers Mark and Bryan accidentally purchased the wrong Chicago house at auction, and now a profit-killing two-family gut job is draining their resources and threatening to bring down their empire. Sean is convinced he can help, but only if he can get his new partners to rethink and restructure.

Chicago real estate broker Berta's ambitious flip was supposed to net six figures, but her off-the-rails project is draining every last cent she's got. She's made mistake after costly mistake and now-unable to turn a profit she's desperate for real estate mogul Sean Conlon to help cut her losses.