Host Kevin O'Connor meets with landscape designer Jenn Nawada Evans to see her plan for the rambling site. The first order of business is reclaiming a good percentage of the backyard from invasive vines and brambles that have been encroaching on the lawn for years. Landscape contractor Roger Cook and his crew make quick work of it using a skid steer loader with a brush hog attachment. General contractor Tom Silva and master carpenter Norm Abram assemble and raise the gable wall for the new family room addition. Then, on the front of the house, Tom and Kevin repair a historic windowsill that has collapsed, while adding new insulation, flashing, and side casings to the opening. At the end of the day, Norm and Kevin demo the old, low ceiling in the ell to see if any head height can be reclaimed for the new kitchen.