Letter from Ora Osterhout from Paul Osterhout. She wrote to tell her brother that she wanted to hear from him more often and what was happening with their family. She told him that Gertrude sent him some money and that their father might be able to send some too. Gertrude has been thinking about attending school in Independence and Ora wrote of a garden that they had started.

Letter from George W. Tyler to Paul Osterhout. Geo wrote to thank Paul profusely for a gift and to update him on his family. Ora, Paul's sister, had been reelected to her position by the Board of Trustees and a Mrs. Osterhout had a fracture and would need crutches. Geo also mentioned crop prospects and other small bits of news.

Letter from C. B. Wade to Paul Osterhout. The letterhead reads that it was from the City National Bank. Wade wrote Paul to inform him of a telegram from John Jeremiah Osterhout's wife about her husband's death. She requested money for funeral arrangements and Wade had it sent to her.

Letter from John Patterson Osterhout to his daughter, Gertrude Osterhout, discussing daily life at home. He mentioned that they would be able to make some money by producing buttermilk and that they would be getting more poultry soon. John's uncle, Peter, was having a birthday soon and he requested that Gertrude write a letter to him so that he may pass it along. The letter closed with John saying that it was his birthday the next day and that he wanted Gertrude and his son, Paul, to write to him.

Certificate of appointment to Postmaster by President Chester Alan Arthur for John Patterson Osterhout. The certificate was signed by the President and the Postmaster General, Walter Q. Gresham. It certified John to work as Postmaster in Belton, Texas.

Letter from John Patterson Osterhout to his mother, Sarah Osterhout. He wrote his mother to let her know how his family was doing. He told her he was sorry to hear that someone was sick and gave his recommendation to have the man inhale smoke to help him. He then went on to write about his beliefs that inhaling smoke was good for the lungs and that he learned this from inhaling smoke from a campfire.

Letter from John Patterson Osterhout to his son, Paul Osterhout, about how glad he is that Paul went to school. John looked forward to seeing Paul and his sister's, Gertrude, educational growth. He expressed worry about his younger son, John Jeremiah, not showing any interest in receiving education.

Postcard from John Patterson Osterhout to his son, Paul Osterhout, regarding finances. John wanted to send his son money to return home, but he had to wait until he had more.

Letter from John Patterson Osterhout to his son, Paul Osterhout, regarding Paul returning home for a visit. John recommended Paul get his certification to practice being a doctor before he graduates. John sent what money he could and if Paul was able, he had a list of people he wanted Paul to try to visit.