The hill country around Judea offered remote terrain to which refugees might flee, but reaching safety could require difficult travel on foot. Ancient houses commonly had flat roofs used as working and living spaces, often reached by exterior stairs. A person on a roof could therefore descend and leave without first moving through the interior to gather belongings.
An outer cloak was a valuable practical possession, especially at night, yet Jesus' illustration says not even to return for it. Winter brought colder weather and seasonal rains that could make roads and wadis difficult. Matthew's reference to the Sabbath reflects the way Sabbath observance structured Jewish communal life and could complicate emergency movement. Pregnancy and nursing would make hurried travel particularly dangerous.