He expanded his family's holdings by selling off land, paying down debt, and starting new businesses. Over the next few years, Surratt acquired or built a carriage house, corn crib, general store, forge, granary, gristmill, stable, tobacco curing house, and wheelwright's shop. The family had enough money to send all three children to nearby Roman Catholic boarding schools. Isaac and John Jr. attended the school at St. Thomas Manor, and Anna enrolled at the Academy for Young Ladies (Mary's alma mater). The family's debts continued to mount, however, and John Sr.'s drinking worsened. John sold another of land in 1856 to pay debts. By 1857, Surratt had sold all but of the family's formerly extensive holdings (which represented about half the he had originally owned). Most of the family's slaves were also sold to pay debts. Still, his alcoholism worsened. In 1858, Mary wrote a letter to her local priest, telling him that Surratt was drunk every single day. In 1860, St. Thomas Manor School closed, and Isaac found work in Baltimore, Maryland. The Surratts sold off another of land, which enabled Anna to remain at the Academy for Young Ladies and for John Jr. to enroll at St. Charles College, Maryland (a Catholic seminary and boarding school in Ellicott's Mills). The couple also borrowed money that same year against their townhouse in Washington, DC, and at some point used the property as collateral for a $1,000 loan.