Alison Victoria and contractor Donovan Eckhardt tackle an 1800s landmarked home in Chicago's Wicker Park neighborhood. They think the home's massive size and profit potential make it a no-brainer, but some major structural issues and a tenant who won't vacate cause them to lose control of the already maxed-out budget.

While looking for a property in Wicker Park, designer Alison Victoria and contractor Donovan Eckhardt discover what seems like a great deal on an 1885 triplex with fire damage. But even as Alison starts picking out some old Chicago pieces to mix in with the new sophisticated design, hidden structural damage from the fire starts burning up their hopes for a profit.

Alison Victoria and Donovan Eckhardt are back in Chicago's Bucktown neighborhood, where they find a Civil War-era house on a corner lot with only 1,200 square feet of living space. Their challenge is to wring enough additional space and fresh design from the small home to get their price point without destroying its original history and charm.