A brief letter from James E. Frear to John Patterson Osterhout concerning legal matters. It appears there is trouble concerning the death of someone and an estate that had no will. James, an attorney, advises that John sue for his share having been used for a time before everything was sorted out. Included is an envelope addressed to "Hon. John Patterson Osterhout."

Letter from James E. Frear to John Patterson Osterhout regarding an inheritance. James told John he was entitled to one tenth of the money a family member would receive for property that was being sold after someone's death.

Letter from Elizabeth to her brother, John Patterson Osterhout, regarding a death in the family. She wrote that she was grateful she had children to take care of her after her husband died and that once the estate was settled, there would not be anything she could use to take care of herself with. Included is an envelope addressed to "Mr. John P. Osterhout."

Letter from Chloe Smith to her uncle, John Patterson Osterhout, discussing the family. She wrote about how she and her mother were coping with the loss of her father. She told him that his son, Paul, had returned home. Included is an envelope addressed to "Mr. J. P. Osterhout."

Extension agreement for Mrs. Loriette C.Redway which secured the payment of a $250.00 bond and extended the time in which the loan amount was to be paid. The agreement states that the principal sum plus interest, 7% per year payable semi-annually, will be due three years from January 1, 1898. Six payment coupons were handwritten at the bottom of the agreement and were to be clipped then taken with payment to the Union Trust Co., where payments would be paid and noted on record. None of the coupons remain attached to the extension agreement.